Herbicidal 1,2,4,6-thiatriazines

ABSTRACT

Compounds of formula (I), in which R 1 , R 2  and R 3  are as defined in claim 1, are                    
     particularly suitable as herbicides.

The present invention relates to novel, herbicidally active thiatriazine derivatives, processes for their preparation, compositions comprising these compounds, and their use for controlling weeds, in particular in crops of useful plants, for example cereals, maize, rice, cotton, soya, oilseed rape, sorghum, sugar cane, sugar beet, sunflower, vegetables and fodder plants, or for inhibiting plant growth.

Thiatriazine compounds are described, for example, in Z. Chem. 15(5), 193-194 (1975), ibid. 15(2), 57-58 (1975), Chem. Ber. 121, 383-386 (1988), Z. Naturforsch. 43, 763-768 (1988), Chem. Ber. 126, 2601-2607 (1993), J. Am. Chem. Soc. 111, 1180-1185 (1989), DD-A-113 006 and in the inaugural dissertation by W. Jürgler, Philipps-University Marburg/Lahn, 1988 (“1λ⁴- and 1λ⁶-2,4,6-thiatriazines from sulfodiimides”).

Novel and simple synthesis methods for preparing novel diversely substituted thiatriazine derivatives have now been found. In addition to the easy accessibility of diversely substituted thiatriazine derivatives, the low number of synthesis stages is another advantage of the synthesis methods. Herbicidal and growth-inhibiting properties have been found for these thiatriazine derivatives.

The present invention thus relates to compounds of the formula I

in which

R₁ is a group —OR₇, —NR₉₀R₉₁ or an N-heterocyclic radical, onto which 1 or 2 further carbocyclic, heterocyclic or aromatic rings can be fused and which contains or does not contain further heteroatoms;

R₇ is C₁-C₁₆alkyl, C₁-C₁₆alkyl substituted by halogen, NO₂, CN, C₁-C₅alkoxy, C₁-C₅alkylthio, C₃-C₈cycloalkoxy, C₃-C₈cycloalkylthio, C₁-C₃trialkylsilyl, C₃-C₁₀alkenyloxy, C₃-C₅alkynyloxy, C₁-C₅alkylcarbonyloxy, C₁-C₃alkoxycarbonyl, C₁-C₃alkylcarbonyl, C₅-C₇cycloalkenyl or C₅-C₇cycloalkenyl substituted by C₁-C₄alkyl, or

R₇ is C₁-C₁₆alkyl substituted by C₃-C₈cycloalkyl, C₆-C₁₂bicycloalkyl, C₆-C₁₂chlorobicycloalkyl, C₆-C₁₂bicycloalkenyl or adamantyl, or

R₇ C₁-C₁₆alkyl substituted by substituted or unsubstituted aryl, aryloxy, arylmethyleneoxy, arylcarbonyl, arylcarbonyloxy or a heterocyclic ring, or

R₇ is C₃-C₁₅alkenyl, C₃-C₁₅alkenyl substituted by halogen, C₁-C₃alkoxy, C₃-C₈cycloalkyl, C₁-C₃trialkylsilyl or substituted or unsubstituted aryl or aryloxy, or

R₇ is C₃-C₅alkynyl, C₃-C₁₂cycloalkyl, C₃-C₁₂cycloalkyl substituted by halogen, CN, C₁-C₃trialkylsilyl, ═O, C₁-C₆alkyl, cyano-C₁-C₅alkyl, C₁-C₅alkyl-CONH—C₁-C₅alkyl, phenyl-CONH—C₁-C₅alkyl, C₁-C₅chloroalkyl, C₁-C₃alkoxy, C₁-C₃alkylthio, C₁-C₃alkoxycarbonyl, C₁-C₃alkoxycarbonyl-C₁-C₅alkyl, C₅-C₇cycloalkyl, C₂-C₄alkenyl, C₂-C₄alkynyl, benzyl or C₁-C₃ halogenoalkyl, or

R₇ is C₅-C₇cycloalkenyl, C₅-C₇cycloalkenyl substituted by C₁-C₃alkyl, or

R₇ is C₆-C₁₂bicycloalkyl, C₆-C₁₂bicycloalkyl substituted by C₁-C₃alkyl, cyano or halogen, C₆-C₁₂bicycloalkenyl, C₆-C₁₂bicycloalkenyl substituted by C₁-C₃alkyl, or

R₇ is a substituted or unsubstituted non-aromatic heterocyclic ring or an alicyclic ring system;

R₉₀ and R₉₁ independently of one another are hydrogen, C₁-C₁₂alkyl, C₁-C₁₂alkyl substituted by halogen, NO₂, CN, hydroxyl, C₁-C₃alkoxy, C₁-C₃alkoxycarbonyl, C₁-C₃trialkylsilyl, C₁-C₆alkylamino, di(C₁-C₆alkyl)amino, C₃-C₇cycloalkyl,

 or a heterocyclic ring, or C₃-C₁₀alkenyl, C₃-C₁₀alkynyl, C₆-C₁₂bicycloalkyl, C₆-C₁₂bicycloalkenyl, C₃-C₁₂cycloalkyl, C₃-C₁₂cycloalkyl substituted by C₁-C₄alkyl, C₅-C₇cycloalkenyl or C₅-C₇cycloalkenyl substituted by C₁-C₄alkyl, with the proviso that R₉₀ and R₉₁ are not simultaneously hydrogen; or

R₉₀ and R₉₁, together with the nitrogen atom to which they are bonded, form a saturated heterocyclic ring which contains 2-12 carbon atoms and can contain, as further heteroatoms, a nitrogen, an oxygen or a sulfur atom and can be substituted by C₁-C₄alkyl, C₁- or C₂halogenoalkyl, C₁- or C₂hydroxyalkyl, methoxy-C₁-C₄alkyl, halogen, hydroxyl, CN, C₁-C₄alkoxy, C₁-C₄alkylcarbonyl, C₁- or C₂halogenoalkyl

 C₁-C₃alkoxycarbonyl, (C₁-C₃alkyl)₂NCO, di(C₁-C₄alkyl)amino or ═O and can additionally be bridged by 1 or 2

 groups and onto which 1 or 2 further carbocyclic, heterocyclic or aromatic rings can be fused, or

R₉₀ and R₉₁, together with the nitrogen atom to which they are bonded, form a mono- or diunsaturated heterocyclic ring which contains 5-7 carbon atoms and is substituted or unsubstituted by C₁-C₄alkyl, C₁- or C₂halogenoalkyl, halogen, hydroxyl, CN, amino, C₁-C₄alkylamino, di(C₁-C₄alkyl)amino, phenyl, C₁-C₄alkoxy or C₁-C₃alkoxycarbonyl and additionally bridged by 1 or 2

 groups and onto which 1 or 2 further carbocyclic, heterocyclic or aromatic rings can be fused;

the radicals R₂₄ independently of one another are hydrogen or methyl;

R₉₈ is hydrogen, fluorine, chlorine, bromine, CN, C₁-C₃alkoxy, C₁-C₃alkoxycarbonyl, C₁-C₃alkoxy-C₁-C₃alkyl, C₁- or C₂halogenoalkyl, C₁-C₅alkyl, NO₂, C₃-C₅alkenyl, cyclopropyl or C₁- or C₂halogenoalkoxy;

R₂ is halogen, C₁-C₁₀alkoxy, C₁-C₁₀alkoxy substituted by halogen, CN, NO₂, C₁-C₆alkoxy, C₁-C₆alkylthio, C₃-C₆alkenyloxy, C₁-C₆alkoxycarbonyl, heterocyclyl or substituted or unsubstituted aryl or aryloxy, C₃-C₁₀alkenyloxy, C₃-C₁₀alkenyloxy substituted by halogen, CN, NO₂, C₁-C₆alkoxy, C₃-C₆alkenyloxy, C₁-C₆alkoxycarbonyl or substituted or unsubstituted aryl or aryloxy, C₁-C₁₀alkylthio, C₁-C₁₀alkylthio substituted by halogen, CN, NO₂, C₁-C₆alkoxy, C₃-C₆alkenyloxy, C₁-C₆alkoxycarbonyl or substituted or unsubstituted aryl or aryloxy, C₃-C₁₀alkenylthio or C₃-C₁₀alkenylthio substituted by halogen, CN, NO₂, C₁-C₆alkoxy, C₃-C₆alkenyloxy, C₁-C₆alkoxycarbonyl or substituted or unsubstituted aryl or aryloxy, or

R₂ is C₃-C₅alkynyloxy, C₃-C₅-alkynylthio, C₃-C₈cycloalkyl-X—, C₆-C₁₂bicycloalkyl-X—, heterocyclyl-X—, alicyclyl-X—, aryl-X—, phthalidyl-X—, biphenyl-X— or heteroaryl-X—;

X is —O—, —S—, —SO— or —SO₂—, or

R₂ is a group R₈₈R₈₉N—,

R₈₈ and R₈₉ independently of one another are hydrogen, C₁-C₆alkyl, C₁-C₆alkyl substituted by halogen, CN, C₁-C₃alkoxy or

 C₃-C₁₂cycloalkyl, C₃-C₁₀alkenyl, C₃-C₁₀alkynyl, C₆-C₁₂bicycloalkyl or C₆-C₁₂bicycloalkyl substituted by C₁-C₃alkyl;

the radicals R₂₀ independently of one another are hydrogen or C₁-C₄alkyl;

n₇ is 4 or 5;

Y is —O—, —S—, —NH— or —NR₁₀₁—;

R₁₀₁ is C₁-C₄alkyl, C₁-C₄alkylcarbonyl or C₁-C₃alkoxycarbonyl; and

R₉₈ is as defined above;

R₃ is halogen, hydroxyl, C₁-C₁₀alkoxy, C₁-C₁₀alkoxy substituted by halogen, CN, NO₂, C₁-C₆alkoxy, C₁-C₆alkylthio, C₃-C₆alkenyloxy, C₁-C₆alkoxycarbonyl, heterocyclyl or substituted or unsubstituted aryl or aryloxy, C₃-C₁₀alkenyloxy, C₃-C₁₀alkenyloxy substituted by halogen, CN, NO₂, C₁-C₆alkoxy, C₃-C₆alkenyloxy, C₁-C₆alkoxycarbonyl or substituted or unsubstituted aryl or aryloxy, C₁-C₁₀alkylthio, C₁-C₁₀alkylthio substituted by halogen, CN, NO₂, C₁-C₆alkoxy, C₃-C₆alkenyloxy, C₁-C₆alkoxycarbonyl or substituted or unsubstituted aryl or aryloxy, C₃-C₁₀alkenylthio or C₃-C₁₀alkenylthio substituted by halogen, CN, NO₂, C₁-C₆alkoxy, C₃-C₆alkenyloxy, C₁-C₆alkoxycarbonyl or substituted or unsubstituted aryl or aryloxy, or

R₃ is C₃-C₅alkynyloxy, C₃-C₅alkynylthio, C₃-C₈cycloalkyl-X—, C₆-C₁₂bicycloalkyl-X—, heterocyclyl-X—, alicyclyl-X—, aryl-X—, phthalidyl-X—, biphenyl-X— or heteroaryl-X—; and

X is as defined above,

and stereoisomers of the compounds of the formula I,

excluding the compounds of formulae I₁ to I₇

wherein

R₀₁ is hydrogen, methyl, ethyl, n-propyl, i-butyl, tert-butyl, allyl, cyclohexyl or benzyl;

R₀₂ is ethyl or benzyl and

R₀₃ is ethyl, cyclohexyl or benzyl, or

R₀₂ and R₀₃, together with the nitrogen atom to which they are bonded, form a piperidine ring;

R₀₄ is chlorine, methylthio, ethylthio, i-propylthio, n-butylthio, i-butylthio, phenylthio or benzylthio;

R₀₅ is ethoxy, methylthio, ethylthio or phenylthio; and

R₀₆ is chlorine or cyclohexylamino.

The alkyl groups occurring in the substituent definitions can be straight-chain or branched, which also applies to the alkyl, alkenyl and alkynyl moiety of the halogenoalkyl, halogenoalkenyl, alkenyloxy, alkylcarbonyloxy, alkoxyalkyl-, alkoxyalkenyl-, alkoxycarbonyl-, alkoxycarbonylalkyl-, alkylamino-, dialkylamino-, alkoxyalkoxy-, nitroalkyl-, cyanoalkyl-, hydroxyalkyl-, alkylaminoalkyl-, dialkylaminoalkyl-, cycloalkylalkyl-, heterocyclylalkyl-, alkoxyalkenyloxy-, alkoxycarbonylalkenyloxy-, halogenoalkylthio-, alkoxyalkylthio-, alkenylthio, halogenoalkenylthio-, alkoxyalkenylthio-, halogenoalkylcarbonyl- and halogenoalkoxycarbonyl groups.

Examples of alkyl groups are methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tetradecyl or hexadecyl and branched isomers thereof. These alkyl groups can be substituted by halogen, cyano, nitro, hydroxyl, C₁-C₃alkoxy, C₁-C₆alkylamino, di(C₁-C₆-alkyl)amino, C₃-C₁₀alkenyl, C₃-C₁₀alkynyl, C₃-C₁₀alkenyloxy, C₃-C₅alkynyloxy, C₁-C₃trialkylsilyl, C₁-C₆alkoxycarbonyl, heterocyclyl, C₃-C₁₂cycloalkyl, C₃-C₈cycloalkoxy or C₆-C₁₀bicycloalkyl. The alkenyl and alkynyl radicals can be mono- or polyunsaturated.

Examples of alkenyls are allyl, methallyl, 1-methylallyl, but-2-en-1-yl, pent-4-en-1-yl, hex-4-en-1-yl and hept-4-en-1-yl, preferably alkenyl radicals having a chain length of 3 to 6 carbon atoms. The alkenyl groups can be substituted on the saturated carbon atoms, for example by C₁-C₆alkoxy or C₃-C₈cycloalkyl, and on the saturated or unsaturated carbon atoms by halogen. The alkenyl radicals are preferably bonded to a heteroatom by a saturated carbon atom.

Examples of alkynyls are propargyl, but-3-yn-1-yl, but-2-yn-1-yl, 1-methylpropargyl, 2-methylbutyn-2-yl, pent-4-yn-1-yl or 2-hexynyl, preferably alkynyl radicals having a chain length of 3 to 6 carbon atoms. The alkynyl radicals are preferably bonded to a heteroatom via a saturated carbon atom.

Halogen is fluorine, chlorine, bromine or iodine, preferably fluorine, chlorine or bromine. A corresponding statement also applies to halogen in combination with other definitions, such as halogenoalkyl, halogenoalkenyl, halogenoalkoxy, halogenoalkylcarbonyl, halogenoalkoxycarbonyl, halogenoalkylcarbonyloxy, halogenocycloalkyl or halogenobicycloalkyl.

Halogenoalkyl is alkyl groups which are mono- or polysubstituted, in particular mono- to trisubstituted, by halogen, halogen specifically being iodine and, in particular, fluorine, chlorine and bromine, for example fluoromethyl, difluoromethyl, trifluoromethyl, chloromethyl, dichloromethyl, trichloromethyl, 2,2,2-trifluoroethyl, 1,1-dichloro-2,2,2-trifluoroethyl, pentafluoroethyl, 2-fluoroethyl, 2-chloroethyl and 2,2,2-trichloroethyl.

Alkoxy is, for example, methoxy, ethoxy, n-propoxy, iso-propoxy, n-butoxy, iso-butoxy, sec-butoxy, tert-butoxy, and one of the isomeric pentoxy, hexyloxy, heptyloxy, octyloxy, nonyloxy and decyloxy radicals.

Halogenoalkenyl is alkenyl groups which are mono- or polysubstituted by halogen, halogen being bromine, iodine and, in particular, fluorine and chlorine, for example 2,2-difluoro-1-methylvinyl, 3-fluoropropenyl, 3-chloropropenyl, 3-bromopropenyl, 2,3,3-trifluoropropenyl and 4,4,4-trifluoro-but-2-en-1-yl. Preferred C₃-C₁₅alkenyl radicals which are mono- di- or trisubstituted by halogen are those which have a chain length of 3 to 6 carbon atoms.

Alkoxycarbonyl is, for example, methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, butoxycarbonyl, pentoxycarbonyl and hexyloxycarbonyl and branched isomers thereof, preferably methoxycarbonyl, ethoxycarbonyl and propoxycarbonyl.

Alkylamino is, for example, methylamino, ethylamino, propyl-, butyl-, pentyl- and hexylamino and their branched isomers.

Dialkylamino is, for example, dimethylamino, methylethylamino, diethylamino, n-propylmethylamino, dipropyl-, dibutyl-, dipentyl- and dihexylamino and their branched isomers.

In substituents such as dialkylamino or dialkylaminoalkyl, the alkyl radicals can be identical or different. They preferably have the same meaning. Corresponding statements also apply to the alkyl radicals in dialkylaminocarbonyl and trialkylsilyl substituents.

Alkoxyalkoxy is, for example, methoxymethoxy, ethoxymethoxy, ethoxyethoxy, propoxymethoxy, propoxyethoxy, butoxyethoxy and butoxybutoxy.

Halogenoalkoxy is, for example, fluoromethoxy, difluoromethoxy, trifluoromethoxy, 2,2,2-trifluorethoxy, 1,1,2,2-tetrafluorethoxy, 2fluorethoxy, 2-chloroethoxy and 2,2,2-trichloroethoxy.

Alkylthio is, for example, methylthio, ethylthio, propylthio, butylthio, pentylthio, hexylthio, heptylthio, octylthio, nonylthio or decylthio and branched isomers thereof.

Alkenyloxy is, for example, allyloxy, 1-methylallyloxy, methallyloxy, but-2-en-1-yloxy or hex-2-en-1-yloxy. Alkenyl radicals having a chain length of 3 to 6 carbon atoms are preferred.

Alkynyloxy is, for example, propargyloxy, 1-methylpropargyloxy, but-3-yn-1-yloxy or pent-4-yn-1-yloxy.

Alkenylthio is, for example, allylthio, methallylthio, but-3-en-1-ylthio, pent-4-en-1-ylthio or hex-2-en-1-ylthio.

Alkynylthio is, for example, propargylthio, 1-methylpropargylthio, but-3-yn-1-ylthio, pent-4-yn-1-ylthio or hex-2-yn-1-ylthio.

Suitable cycloalkyl substituents contain 3 to 12 carbon atoms and are, for example, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl or cyclododecyl. Corresponding cycloalkenyl substituents can be mono- or else polyunsaturated, for example cyclopentenyl, cyclopentadienyl, cyclohexenyl, cycloheptenyl or cyclooctatetraenyl.

Cycloalkyl and also cycloalkenyl substituents can, unless stated otherwise, be substituted by C₁-C₄alkyl and contain fused-on aryl rings.

If alkyl, alkenyl or alkynyl occur as substituents on a cycloalkyl, cycloalkenyl, bicycloalkyl, bicycloalkenyl, phenyl, biphenyl, naphthyl or heterocyclyl, these ring systems can also be polysubstituted by alkyl, alkenyl or alkynyl.

If R₂₀, R₂₄, R₂₅, R₉₇, R₉₈ or R₉₉ occur on phenyl, naphthyl or heteroaryl, these ring systems can also be polysubstituted by R₂₀, R₂₄, R₂₅, R₉₇, R₉₈ or R₉₉.

If R₂₀, R₂₄, R₂₅, R₉₈ or R₁₀₀ occur on alicyclic or carbocyclic rings, these ring systems can also be polysubstituted by R₂₀, R₂₄, R₂₅, R₉₈ or R₁₀₀.

Carbocyclic radicals are to be understood as meaning saturated and unsaturated, mono- and polycyclic ring systems which consist of cycloalkanes, cycloalkenes, polycycloalkanes and polycycloalkenes. Carbocyclic radicals preferably contain 3 to 12 carbon atoms, for example cyclopropane, cyclobutane, cyclopentane, cyclohexane, cyclohexene, cycloheptane, cyclooctane, cyclononane, cyclodecane, cyclododecane and cis- and trans-decalin, it being possible for these carbocyclic radicals, unless stated otherwise, to be substituted by C₁-C₄alkyl.

Heterocyclyl is to be understood as meaning mono- and polycyclic ring systems which, in addition to carbon atoms, contain at least one heteroatom, such as nitrogen, oxygen or sulfur. They can be saturated or unsaturated and substituted by C₁-C₃alkyl, halogen or ═O. Such ring systems preferably contain 3 to 12 ring atoms. This also applies to those heterocyclic radicals which, as in the case of groups such as —NR₉₀R₉₁, are formed by 2 substituents bonded to a nitrogen atom.

Examples of N-heterocyclic radicals onto which 1 or 2 further carbocyclic, heterocyclic or aromatic rings can be fused or spiro-bonded and which contain or do not contain further heteroatoms, in the definition of R₁, are:

in which the radicals R₂₀ independently of one another are hydrogen, C₁-C₄alkyl or C₁-C₃alkoxy;

R₂₅ is hydrogen, chlorine, methyl or methoxy;

R₁₀₀ is hydrogen or C₁-C₃alkyl;

Y, is —O—, —S— or —NR₃₀;

R₃₀ is hydrogen, methyl, C₁-C₃alkylcarbonyl or (C₁-C₃alkyl)₂NCO—;

n₁ is 1, 2, 3, 4 or 5;

n₂ is 0, 1 or 2; and

n₃ is a number from 3 to 10. The hetererocyclic radical is bonded to the thiatriazine ring via its nitrogen atom.

Examples of aryl, aryloxy, arylmethyleneoxy, arylcarbonyl-, arylcarbonyloxy or aryloxycarbonyl ring systems in the definition of R₂, R₃, R₇, R₁₃, R₉₄ and R₉₇ are:

in which R₂₅ is as defined above;

R₉₉ is hydrogen, halogen, NO₂, CN, C₁-C₅alkyl, C₁-C₆alkoxy, C₁- or C₂halogenoalkoxy, C₁-C₆-alkenyloxycarbonyl, C₁-C₃alkylthio,

 C₁-C₆alkoxycarbonyl, NH₂, C₁-C₃alkyl-CONH, di(C₁-C₆alkyl)amino or C₁-C₆alkylamino;

R₉₈ is hydrogen, fluorine, chlorine, bromine, CN, C₁-C₃alkoxy, C₁-C₃alkoxycarbonyl, C₁-C₃-alkoxy-C₁-C₃-alkyl, C₁- or C₂-halogenoalkyl, C₁-C₅-alkyl, NO₂, C₃-C₅alkenyl, cyclopropyl or C₁- or C₂halogenoalkoxy; and

n₆ is 3, 4, 5 or 6.

Examples of heterocyclic rings R₇ and R₂ or R₃ bonded to alkyl or alkoxy are:

in which R₉₈ and R₁₀₀ are as defined above;

R₂₄ is hydrogen or methyl; and

R₁₀₁ is C₁-C₄alkyl, C₁-C₄alkylcarbonyl or C₁-C₃-alkoxycarbonyl.

Examples of non-aromatic heterocyclic rings in the definition of R₇ are:

in which R₁₀₀ and R₁₀₁ are as defined above.

Alicyclic ring systems in the definition of P₇ are saturated and unsaturated, mono- and polycyclic ring systems containing bridge bonds and heteroatoms, such as nitrogen, oxygen or sulfur. Examples of such alicyclic ring systems are:

in which R₂₁ and R₂₂ independently of one another are hydrogen or C₁-C₄alkyl;

n₉ is 3 or 4; and

R₂₀, R₂₄, R₂₅, R₉₈, R₁₀₀, R₁₀₁ and n₆ are as defined above.

Examples of heterocyclic rings R₉₀ and R₉₁, which are independent of one another, bonded to alkyl are:

in which R₂₅ and R₁₀₀ are as defined above.

Saturated and unsaturated and substituted or unsubstituted mono- or bicyclic heterocyclic radicals formed from —NR₉₀R₉₁ include, for example, pyrrolidyl, dimethylpyrrolidyl, piperidyl, morpholinyl, dimethylmorpholinyl, thiomorpholinyl, cis- and trans-decahydro(iso)quinolyl, tetrahydropyridyl, 1,2,3,4-tetrahydro(iso)quinolyl, 1-methylpiperazinyl, perhydroindolyl, 3-pyrrolinyl, hexahydro-azepinyl, aziridyl, azeudyl, 4-piperidonyl and homopiperazinyl, it being possible for these heterocyclic radicals to have 1 or 2 further carbocyclic, heterocyclic or aromatic rings, for example cyclohexane, (nor-)bornane, cyclopentane, cycloheptane, cyclododecane or phenyl, fused-on or spiro-linked carbocyclic rings, for example cyclohexane or (nor-)bornene.

Further examples of saturated, substituted or unsubstituted heterocyclic rings formed from —NR₉₀R₉₁ which contain or do not contain heteroatoms or which can additionally be bridged with 1 or 2 groups

 are:

Preferred examples in which R₉₀ and R₉₁, together with the nitrogen atom, form a ring are pyrrolidyl, piperidyl, dimethylpiperidyl, ethoxycarbonylpiperidyl, morpholinyl, dimethylmorpholinyl, cis- and trans-decahydro(iso)quinolyl and 1,2,3,4-tetrahydro(iso)quinolyl.

Examples of aryl-X—, phthalidyl-X—, biphenyl-X— or heteroaryl-X— R₂ and R₃ are:

in which X is —O—, —S—, —SO— or —SO₂—;

X₂ is —O—, —S— or —NR₁₀₀—;

R₂₀, R₂₄, R₉₈ and R₁₀₀ are as defined above;

R₉₂ is hydrogen or C₁-C₄alkyl;

R₉₃ is hydrogen, C₁-C₄alkyl, hydroxyl, C₁-C₄alkoxy or C₁-C₄alkylthio; R₉₇ is hydrogen, halogen, NO₂, CN, C₃-C₆cycloalkoxy, C₁-C₁₀alkyl, C₁-C₁₀alkyl substituted by halogen, CN, NO₂, C₁-C₆alkoxy, C₃-C₆alkenyloxy, C₁-C₆alkoxycarbonyl or substituted or unsubstituted aryl or aryloxy, C₃-C₁₀alkenyl, C₃-C₁₀alkenyl substituted by halogen, CN, NO₂, C₁-C₆alkoxy, C₃-C₆alkenyloxy, C₁-C₆alkoxycarbonyl or substituted or unsubstituted aryl or aryloxy, C₁-C₁₀alkoxy, C₁-C₁₀alkoxy substituted by halogen, CN, NO₂, C₁-C₆alkoxy, C₃-C₆alkenyloxy, C₁-C₆alkoxycarbonyl or substituted or unsubstituted aryl or aryloxy, C₃-C₁₀alkenyloxy, C₃-C₁₀alkenyloxy substituted by halogen, CN, NO₂, C₁-C₆alkoxy, C₃-C₆alkenyloxy, C₁-C₆-alkoxycarbonyl or substituted or unsubstituted aryl or aryloxy, C₁-C₁₀alkylcarbonyl, C₁-C₁₀alkylcarbonyl substituted by halogen, CN, NO₂, C₁-C₆alkoxy, C₃-C₆alkenyloxy, C₁-C₆alkoxycarbonyl or substituted or unsubstituted aryl or aryloxy, C₁-C₁₀alkoxycarbonyl, C₁-C₁₀alkoxycarbonyl substituted by halogen, CN, NO₂, C₁-C₆alkoxy, C₃-C₆alkenyloxy, C₁-C₆alkoxycarbonyl or substituted or unsubstituted aryl or aryloxy, C₁-C₁₀alkylcarbonyloxy or C₁-C₁₀alkylcarbonyloxy substituted by halogen, CN, NO₂, C₁-C₆alkoxy, C₃-C₆alkenyloxy, C₁-C₆alkoxycarbonyl or substituted or unsubstituted aryl or aryloxy, or R₉₇ is CHO, C₃-C₈-cycloalkyl, C₁-C₄alkylthio, C₃- or C₄alkenylthio, (R₉₄)₂N—, (R₉₅)₂N—CO—, aryl, aryloxy, arylcarbonyl or aryloxycarbonyl, or a group

 the radicals R₉₄ independently of one another are hydrogen, C₁-C₁₀alkyl, C₃-C₈cycloalkyl, C₁-C₁₀alkylcarbonyl or substituted or unsubstituted arylcarbonyl;

the radicals R₉₅ independently of one another are hydrogen, C₁-C₅alkyl or C₃-C₈cycloalkyl;

and n is a number from 5 to 12.

Examples of alicyclyl-X— R₂ and R₃ are:

in which R₂₀, R₂₄, R₂₅, R₉₈, R₁₀₀, R₁₀₁, X, n₆ and n₉ are as defined above.

Examples of nonaromatic heterocyclyl-X— R₂ and R₃ are:

in which R₂₄, X, R₁₀₀ and R₁₀₁ are as defined above.

Examples of cyclic radicals R₁₁, in the compounds of the formula XII in the preparation process, onto which 1 or 2 further carbocyclic, heterocyclic or aromatic rings can be fused and which contain or do not contain heteroatoms are:

In the definitions cyanoalkyl, alkoxycarbonyl, alkylcarbonyloxy, alkylcarbonyl, alkoxycarbonylalkoxy and alkenyloxycarbonyl, the cyano or carbonyl carbon atom is not included in the particular lower and upper limits stated for the number of carbons.

Unless stated specifically, ¹H— and ¹³C-NMR spectra (Tables 1-6) were recorded with a 300 MHz spectrometer in CDCl₃.

The compounds of the formula I in which R₂ and R₃ differ from one another have a centre of asymmetry in the sulfur atom of the thiatriazine ring.

Furthermore, asymmetric centres can be present in the substituents of the thiatriazine ring, for example in the definition of R₁ or R₇. This means that diastereomers can be formed, which can sometimes be separated by column chromatography, as shown, for example, in the tabular examples Compound Nos. 5.45/5.46, 6.6, 6.10, 6.55/6.56, 6.92/6.93, 6.120/6.121 and 6.153/6.154.

If substituents are bonded via a wavy line to a ring system in the formulae, for example in the definition of R₁, this means that all conformations or geometric isomerisms (‘up’ and ‘down’, or ‘equatorial’ and ‘axial’) are possible for these substituents.

Unless chiral starting materials are used, the compounds of the formula I are in general obtained as racemates in the process described in this application, and these are separated by customary separation processes, for example chromatographic processes, for example high pressure liquid chromatography (HPLC) over acetylcellulose, on the basis of physico-chemical properties. In the present invention, the active compounds of the formula I are to be understood as meaning both the pure optical antipodes and the racemates. Unless the individual optical antipodes are referred to specifically, those racemic mixtures which are formed in the preparation process described are to be understood under the formula given. If an aliphatic C═C double bond is present or if alicyclic or carbocyclic rings contain substituents, geometric isomerism may also occur.

The formula I is intended to include all these possible isomers, enantiomers and diastereoisomers and mixtures thereof.

Preferred compounds are those of the formula I

in which the radicals R₂₀, R₂₅, R₁₀₀, Y₁, n₁, n₂ and n₃ are as defined above.

Suitable substituted or unsubstituted bicycloalkyl and bicycloalkenyl substituents contain 6 to 12 carbon atoms and are, for example:

in which R₂₄ is as defined above.

The substituents in composite definitions, for example cycloalkoxy, cycloalkylalkyl, cycloalkyl-X—, bicycloalkylalkyl, bicycloalkyl-X—, alkylcarbonyl, alkylcarbonyloxy, cycloalkylalkenyl, cycloalkenylalkyl, alkoxyalkyl, alkoxyalkenyl, halogenobicycloalkyl, alkenyloxycarbonyl, alkenyloxyalkoxy, alkoxycarbonylalkoxy, alkylaminoalkyl, dialkylaminoalkyl, heterocyclylalkyl, heterocyclyl-X—, halogenoalkenyloxy, alkoxyalkenyloxy, alkenyloxyalkenyloxy, alkoxycarbonylalkenyloxy, halogenoalkylthio, alkenyloxyalkylthio, alkoxycarbonylalkylthio, halogenoalkenylthio, alkoxyalkenylthio, alkenyloxyalkenylthio, alkoxycarbonylalkenylthio, halogenoalkylcarbonyl, alkoxyalkylcarbonyl, alkenyloxyalkylcarbonyl, alkoxycarbonylalkylcarbonyl, halogenoalkoxycarbonyl, alkoxyalkoxycarbonyl, alkenyloxyalkoxycarbonyl, alkoxycarbonylalkoxycarbonyl, halogenoalkylcarbonyloxy, alkoxyalkylcarbonyloxy, alkenyloxyalkoxycarbonyloxy and alkoxycarbonylalkylcarbonyloxy can also be assigned corresponding definitions.

in which

R₁ is a group —OR₇, —NR₉₀R₉₁, or an N-heterocyclic radical, onto which 1 or 2 further carbocyclic, heterocyclic or aromatic rings can be fused and which contains or does not contain further heteroatoms;

R₇ is C₁-C₁₆alkyl, C₁-C₁₆alkyl substituted by halogen, NO₂, CN, C₁-C₅alkoxy, C₁-C₅alkylthio, C₃-C₈cycloalkoxy, C₁-C₃trialkylsilyl, C₃-C₁₀alkenyloxy, C₃-C₅alkynyloxy, C₁-C₅alkyl-carbonyloxy, C₁-C₃alkoxycarbonyl, C₁-C₃alkylcarbonyl, C₅-C₇cycloalkenyl or C₅-C₇cycloalkenyl substituted by C₁-C₄alkyl, or

R₇ is C₁-C₁₆alkyl substituted by C₃-C₈cycloalkyl, C₆-C₁₂bicycloalkyl, C₆-C₁₂chlorobicycloalkyl, C₆-C₁₂bicycloalkenyl or adamantyl, or

R₇ is C₁-C₁₆alkyl substituted by substituted or unsubstituted aryl, aryloxy, arylmethyleneoxy, arylcarbonyl, arylcarbonyloxy or a heterocyclic ring, or

R₇ is C₃-C₁₅alkenyl, C₃-C₁₅alkenyl substituted by halogen, C₁-C₃alkoxy, C₃-C₈cycloalkyl or substituted or unsubstituted aryl or aryloxy, or

R₇ is C₃-C₅alkynyl, C₃-C₁₂cycloalkyl, C₃-C₁₂cycloalkyl substituted by halogen, CN, C₁-C₃-trialkylsilyl, ═O, C₁-C₆alkyl, cyano-C₁-C₅alkyl, C₁-C₅alkyl-CONH—C₁-C₅alkyl, phenyl-CONH—C₁-C₅alkyl, C₁-C₅chloroalkyl, C₁-C₃alkoxy, C₁-C₃alkylthio, C₁-C₃alkoxycarbonyl, C₁-C₃alkoxycarbonyl-C₁-C₅alkyl, C₅-C₇cycloalkyl, C₂-C₄alkenyl, C₂-C₄alkynyl, benzyl or C₁-C₃halogenoalkyl, or

R₇ is C₅-C₇cycloalkenyl, C₅-C₇cycloalkenyl substituted by C₁-C₃alkyl, or

R₇ is C₆-C₁₂bicycloalkyl, C₆-C₁₂bicycloalkyl substituted by C₁-C₃alkyl or halogen, C₆-C₁₂bicycloalkenyl, C₆-C₁₂bicycloalkenyl substituted by C₁-C₃alkyl, or

R₇ is a substituted or unsubstituted nonaromatic heterocyclic ring or an alicyclic ring system;

R₉₀ and R₉₁ independently of one another are hydrogen, C₁-C₁₂alkyl, C₁-C₁₂alkyl substituted by halogen, NO₂, CN, hydroxyl, C₁-C₃alkoxy, C₁-C₃trialkylsilyl, C₁-C₆alkylamino, di(C₁-C₆-alkyl)amino, C₃-C₇cycloalkyl,

 or a heterocyclic ring, or C₃-C₁₀alkenyl, C₃-C₁₀alkynyl, C₆-C₁₂bicycloalkyl, C₆-C₁₂bicycloalkenyl, C₃-C₁₂cycloalkyl, C₃-C₁₂cycloalkyl substituted by C₁-C₄alkyl, C₅-C₇cycloalkenyl or C₅-C₇cycloalkenyl substituted by C₁-C₄alkyl, with the proviso that R₉₀ and R₉₁ are not simultaneously hydrogen; or

R₉₀ and R₉₁, together with the nitrogen atom to which they are bonded, form a saturated heterocyclic ring which contains 2-12 carbon atoms and can contain, as further heteroatoms, a nitrogen, an oxygen or a sulfur atom and can be substituted by C₁-C₄alkyl, C₁- or C₂-halogenoalkyl, methoxy-C₁-C₄alkyl, halogen, hydroxyl, CN, C₁-C₄alkoxy, C₁-C₄-alkylcarbonyl, C₁- or C₂halogenoalkyl,

 C₁-C₃alkoxycarbonyl, (C₁-C₃alkyl)₂NCO, di(C₁-C₄alkyl)amino or ═O and can additionally be bridged by 1 or 2

 groups and onto which 1 or 2 further carbocyclic, heterocyclic or aromatic rings can be fused, or

R₉₀ and R₉₁, together with the nitrogen atom to which they are bonded, form a monounsaturated heterocyclic ring which contains 5-7 carbon atoms and is substituted or unsubstituted by C₁-C₄alkyl, C₁- or C₂halogenoalkyl, halogen, hydroxyl, CN, amino, C₁-C₄alkylamino, di(C₁-C₄alkyl)amino, phenyl, C₁-C₄alkoxy or C₁-C₃alkoxycarbonyl and is additionally bridged by 1 or 2

 groups and onto which 1 or 2 further carbocyclic, heterocyclic or aromatic rings can be fused;

the radicals R₂₄ independently of one another are hydrogen or methyl;

R₉₈ is hydrogen, fluorine, chlorine, bromine, CN, C₁-C₃alkoxy, C₁-C₃alkoxycarbonyl, C₁-C₃-alkoxy-C₁-C₃alkyl, C₁- or C₂halogenoalkyl, C₁-C₅alkyl, NO₂, C₃-C₅alkenyl, cyclopropyl or C₁- or C₂halogenoalkoxy;

R₂ is halogen, C₁-C₁₀alkoxy, C₁-C₁₀alkoxy substituted by halogen, CN, NO₂, C₁-C₆alkoxy, C₁-C₆alkylthio, C₃-C₆alkenyloxy, C₁-C₆alkoxycarbonyl, heterocyclyl or substituted or unsubstituted aryl or aryloxy, C₃-C₁₀alkenyloxy, C₃-C₁₀alkenyloxy substituted by halogen, CN, NO₂, C₁-C₆alkoxy, C₃-C₆alkenyloxy, C₁-C₆alkoxycarbonyl or substituted or unsubstituted aryl or aryloxy, C₁-C₁₀alkylthio, C₁-C₁₀alkylthio substituted by halogen, CN, NO₂, C₁-C₆alkoxy, C₃-C₆alkenyloxy, C₁-C₆alkoxycarbonyl or substituted or unsubstituted aryl or aryloxy, C₃-C₁₀alkenylthio or C₃-C₁₀alkenylthio substituted by halogen, CN, NO₂, C₁-C₆alkoxy, C₃-C₆alkenyloxy, C₁-C₆alkoxycarbonyl or substituted or unsubstituted aryl or aryloxy, or

R₂ is C₃-C₅alkynyloxy, C₃-C₅alkynylthio, C₃-C₈cycloalkyl-X—, C₆-C₁₂bicycloalkyl-X—, heterocyclyl-X—, alicyclyl-X—, aryl-X—, phthalidyl-X—, biphenyl-X— or heteroaryl-X—; X is —O—, —S—, —SO— or —SO₂—, or

R₂ is a group R₈₈R₈₉N—,

R₈₈ and R₈₉ independently of one another are hydrogen, C₁-C₆alkyl, C₁-C₆alkyl substituted by halogen, CN, C₁-C₃alkoxy or

 C₃-C₁₂cycloalkyl, C₃-C₁₀alkenyl, C₃-C₁₀alkynyl, C₆-C₁₂bicycloalkyl or C₆-C₁₂bicycloalkyl substituted by C₁-C₃alkyl;

the radicals R₂₀ independently of one another are hydrogen or C₁-C₄alkyl;

n₇ is 4 or 5;

Y is —O—, —S—, —NH— or —NR₁₀₁—;

R₁₀₁ is C₁-C₄alkyl, C₁-C₄alkylcarbonyl or C₁-C₃alkoxycarbonyl and

R₉₈ is as defined above; and

R₃ is halogen, C₁-C₁₀alkoxy, C₁-C₁₀alkoxy substituted by halogen, CN, NO₂, C₁-C₆alkoxy, C₁-C₆alkylthio, C₃-C₆alkenyloxy, C₁-C₆alkoxycarbonyl, heterocyclyl or substituted or unsubstituted aryl or aryloxy, C₃-C₁₀alkenyloxy, C₃-C₁₀alkenyloxy substituted by halogen, CN, NO₂, C₁-C₆alkoxy, C₃-C₆alkenyloxy, C₁-C₆alkoxycarbonyl or substituted or unsubstituted aryl or aryloxy, C₁-C₁₀alkylthio, C₁-C₁₀alkylthio substituted by halogen, CN, NO₂, C₁-C₆alkoxy, C₃-C₆alkenyloxy, C₁-C₆alkoxycarbonyl or substituted or unsubstituted aryl or aryloxy, C₃-C₁₀alkenylthio or C₃-C₁₀alkenylthio substituted by halogen, CN, NO₂, C₁-C₆alkoxy, C₃-C₆alkenyloxy, C₁-C₆alkoxycarbonyl or substituted or unsubstituted aryl or aryloxy, or

R₃ is C₃-C₅alkynyloxy, C₃-C₅alkynylthio, C₃-C₈cycloalkyl-X—, C₆-C₁₂bicycloalkyl-X—, heterocyclyl-X—, alicyclyl-X—, aryl-X—, phthalidyl-X—, biphenyl-X— or heteroaryl-X—; and X is as defined above.

Preferred compounds of the formula I are also those in which

in which the radicals R₂₀ independently of one another are hydrogen or C₁-C₄alkyl;

R₂₅ is hydrogen, chlorine, methyl or methoxy;

R₁₀₀ is hydrogen or C₁-C₃alkyl;

Y₁ is —O—, —S— or —NR₃₀;

R₃₀ is hydrogen, methyl, C₁-C₃alkylcarbonyl or (C₁-C₃alkyl)₂NCO;

n₁ is 1, 2, 3, 4 or 5;

n₂ is 0, 1 or 2; and

n₃ is a number from 3 to 10.

Preferred compounds of the formula I are also those in which

R₁ is the group —OR₇, in which

R₇ is as defined under formula I and

R₂ and R₃ independently of one another are chlorine, C₁-C₁₀alkoxy, C₁-C₁₀alkoxy substituted by halogen, CN, NO₂, C₁-C₆alkoxy, C₁-C₆alkylthio, C₃-C₆alkenyloxy, C₁-C₆alkoxycarbonyl, heterocyclyl or substituted or unsubstituted aryl or aryloxy, C₃-C₁₀alkenyloxy, C₃-C₁₀alkenyloxy substituted by halogen, CN, NO₂, C₁-C₆alkoxy, C₃-C₆alkenyloxy, C₁-C₆alkoxycarbonyl or substituted or unsubstituted aryl or aryloxy, C₁-C₁₀alkylthio, C₁-C₁₀alkylthio substituted by halogen, CN, NO₂, C₁-C₆alkoxy, C₃-C₆alkenyloxy, C₁-C₆alkoxycarbonyl or substituted or unsubstituted aryl or aryloxy, C₃-C₁₀alkenylthio or C₃-C₁₀alkenylthio substituted by halogen, CN, NO₂, C₁-C₆alkoxy, C₃-C₆alkenyloxy, C₁-C₆alkoxycarbonyl or substituted or unsubstituted aryl or aryloxy, or R₂ and R₃ independently of one another are C₃-C₅alkynyloxy, C₃-C₅alkynylthio, C₃-C₈cycloalkyl-X—, C₆-C₁₂bicycloalkyl-X—, heterocyclyl-X—, alicyclyl-X—, aryl-X—, phthalidyl-X—, biphenyl-X— or heteroaryl-X—.

Compounds of the formula I which are likewise preferred are those in which

R₁ is the group —OR₇;

R₂ is a group R₈₈R₈₉N—,

 and R₃ is aryl-X—,

phthalidyl-X—, biphenyl-X—, or heteroaryl-X—, in which

R₇, R₂₀, R₈₈, R₈₉, Y, n₇ and X are as defined under formula I.

Thiatriazine derivatives of the formula I which are furthermore preferred are those in which R₁ is a group —NR₉₀R₉₁ or an N-heterocyclic radical, onto which 1 or 2 further carbocyclic, heterocyclic or aromatic rings can be fused and which contains or does not contain further heteroatoms.

R₂ is a group R₈₈R₈₉N—,

 and R₃ is aryl-X—, phthalidyl-X—, biphenyl-X— or heteroaryl-X—, in which R₂₀, R₈₈, R₈₉, Y, n₇ and X are as defined under formula I.

Particularly preferred thiatriazine derivatives of the formula I are those in which

R₁ is a group —OR₇;

R₇ C₁-C₁₆alkyl, C₁-C₁₆alkyl substituted by halogen, NO₂, CN, C₁-C₅alkoxy, C₁-C₅alkylthio, C₃-C₈cycloalkoxy, C₁-C₃trialkylsilyl, C₃-C₁₀alkenyloxy, C₃-C₅alkynyloxy, C₁-C₅alkylcarbonyloxy, C₁-C₃alkoxycarbonyl, C₁-C₃alkylcarbonyl, C₅-C₇cycloalkenyl or C₅-C₇cycloalkenyl substituted by C₁-C₄alkyl, or

R₇ is C₁-C₁₆alkyl substituted by C₆-C₁₂bicycloalkyl, C₆-C₁₂chlorobicycloalkyl,

C₆-C₁₂bicycloalkenyl or adamantyl, or R₇ is C₁-C₁₆alkyl substituted by

in which R₂₄ is hydrogen or methyl;

R₉₈ is hydrogen, fluorine, chlorine, bromine, CN, C₁-C₃alkoxy, C₁-C₃alkoxycarbonyl, C₁-C₃alkoxy-C₁-C₃alkyl, C₁- or C₂halogenoalkyl, C₁-C₅alkyl, NO₂, C₃-C₅alkenyl, cyclopropyl or C₁- or C₂halogenoalkoxy;

R₉₉ is hydrogen, halogen, NO₂, CN, C₁-C₅alkyl, C₁-C₆alkoxy, C₁-C₆alkenyloxycarbonyl, C₁-C₃alkylthio,

 C₁-C₆alkoxycarbonyl, NH₂, C₁-C₃alkyl-CONH, di(C₁-C₆alkyl)amino or C₁-C₆alkylamino;

R₁₀₀ is hydrogen or C₁-C₃alkyl; and

R₁₀₁ is C₁-C₄alkyl, C₁-C₄alkylcarbonyl or C₁-C₃alkoxycarbonyl; or

R₇ is C₃-C₁₂cycloalkyl, C₃-C₁₂cycloalkyl substituted by halogen, CN, C₁-C₃trialkylsilyl, ═O, C₁-C₆alkyl, cyano-C₁-C₅alkyl, C₁-C₅alkyl-CONH—C₁-C₅alkyl, phenyl-CONH—C₁-C₅alkyl, C₁-C₅chloroalkyl, C₁-C₃alkoxy, C₁-C₃alkylthio, C₁-C₃alkoxycarbonyl, C₁-C₃alkoxycarbonyl-C₁-C₅alkyl, C₅-C₇cycloalkyl, C₂-C₄alkenyl, C₂-C₄alkynyl, benzyl or C₁-C₃halogenoalkyl, C₅-C₇-cycloalkenyl or C₅-C₇cycloalkenyl substituted by C₁-C₃alkyl, or

R₇ is C₆-C₁₂bicycloalkyl, C₆-C₁₂bicycloalkyl substituted by C₁-C₃alkyl or halogen,

C₆-C₁₂bicycloalkenyl or C₆-C₁₂bicycloalkenyl substituted by C₁-C₃alkyl, or

R₇ is a substituted or unsubstituted nonaromatic heterocyclic ring or an alicyclic ring system;

R₂ is a group R₈₈R₈₉N—;

R₈₈ and R₈₉ independently of one another are hydrogen, C₁-C₆alkyl, C₁-C₆alkyl substituted by halogen, CN, C₁-C₃alkoxy or

 C₃-C₁₂cycloalkyl, C₃-C₁₀alkenyl,

C₃-C₁₀alkynyl, C₆-C₁₂bicycloalkyl or C₆-C₁₂bicycloalkyl substituted by C₁-C₃alkyl; and

R₃ is aryl-X—, phthalidyl-X—, biphenyl-X— or heteroaryl-X—.

Of these, especially preferred thiatriazine derivatives of the formula I are those in which

R₇ is C₃-C₁₂cycloalkyl, C₃-C₁₂cycloalkyl substituted by halogen, CN, C₁-C₆alkyl, cyano-C₁-C₅alkyl, C₁-C₃alkoxy or C₁-C₃halogenoalkyl, or R₇ is C₅-C₇cycloalkenyl or C₅-C₇cyclo-alkenyl substituted by methyl, or

R₇ is C₆-C₁₂bicycloalkyl, C₆-C₁₂bicycloalkyl substituted by methyl or chlorine,

C₆-C₁₂bicycloalkenyl or C₆-C₁₂bicycloalkenyl substituted by methyl, or

in which

R₁₀₀ is hydrogen or C₁-C₃alkyl; and

R₁₀₁ is C₁-C₄alkyl, C₁-C₄alkylcarbonyl or C₁-C₃alkoxycarbonyl; or

in which R₂₀ is hydrogen or C₁-C₄alkyl;

R₂₁ and R₂₂ independently of one another are hydrogen or C₁-C₄alkyl;

R₂₄ is hydrogen or methyl;

R₂₅ is hydrogen, chlorine, methyl or methoxy;

R₉₈ is hydrogen, fluorine, chlorine, bromine, CN, C₁-C₃alkoxy, C₁-C₃alkoxycarbonyl, C₁-C₃alkoxy-C₁-C₃alkyl, C₁- or C₂halogenoalkyl, C₁-C₅alkyl, NO₂, C₃-C₅alkenyl, cyclopropyl or C₁- or C₂-halogenoalkoxy;

n₆ is 3, 4, 5 or 6;

n₉ is 3 or 4; and

R₁₀₀ and R₁₀₁ are as defined above;

R₂ is a group R₈₈R₈₉N—;

R₈₈ and R₈₉ independently of one another are hydrogen or C₁-C₆alkyl and

in which X is —O— or —S—;

X₂ is —O—, —S— or —NR₁₀₀—;

R₂₀, R₂₄ and R₁₀₀ are as defined above;

R₉₂ is hydrogen or C₁-C₄alkyl;

R₉₃ is hydrogen, C₁-C₄alkyl, hydroxyl, C₁-C₄alkoxy or C₁-C₄alkylthio;

R₉₇ is hydrogen, halogen, NO₂, CN, C₃-C₆cycloalkoxy, C₁-C₁₀alkyl, C₁-C₁₀calkyl substituted by halogen, CN, NO₂, C₁-C₆alkoxy, C₃-C₆alkenyloxy, C₁-C₆alkoxycarbonyl or substituted or unsubstituted aryl or aryloxy, C₃-C₁₀alkenyl, C₃-C₁₀alkenyl substituted by halogen, CN, NO₂, C₁-C₆alkoxy, C₃-C₆alkenyloxy, C₁-C₆alkoxycarbonyl or substituted or unsubstituted aryl or aryloxy, C₁-C₁₀alkoxy, C₁-C₁₀alkoxy substituted by halogen, CN, NO₂, C₁-C₆alkoxy, C₃-C₆alkenyloxy, C₁-C₆alkoxycarbonyl or substituted or unsubstituted aryl or aryloxy, C₃-C₁₀alkenyloxy, C₃-C₁₀alkenyloxy substituted by halogen, CN, NO₂, C₁-C₆alkoxy, C₃-C₆alkenyloxy, C₁-C₆alkoxycarbonyl or substituted or unsubstituted aryl or aryloxy, C₁-C₁₀alkylcarbonyl, C₁-C₁₀alkylcarbonyl substituted by halogen, CN, NO₂, C₁-C₆alkoxy, C₃-C₆alkenyloxy, C₁-C₆alkoxycarbonyl or substituted or unsubstituted aryl or aryloxy, C₁-C₁₀alkoxycarbonyl, C₁-C₁₀alkoxycarbonyl substituted by halogen, CN, NO₂, C₁-C₆alkoxy, C₃-C₆alkenyloxy, C₁-C₆alkoxycarbonyl or substituted or unsubstituted aryl or aryloxy, C₁-C₁₀alkylcarbonyloxy or C₁-C₁₀alkylcarbonyloxy substituted by halogen, CN, NO₂, C₁-C₆-alkoxy, C₃-C₆alkenyloxy, C₁-C₆alkoxycarbonyl or substituted or unsubstituted aryl or aryloxy, or

R₉₇ is CHO, C₃-C₈cycloalkyl, C₁-C₄alkylthio, C₃- or C₄alkenylthio, (R₉₄)₂N—, (R₉₅)₂N—CO—, aryl, aryloxy, arylcarbonyl or aryloxycarbonyl, or a group

 the radicals R₉₄ independently of one another are hydrogen, C₁-C₁₀alkyl, C₃-C₈cycloalkyl, C₁-C₁₀alkylcarbonyl or substituted or unsubstituted arylcarbonyl; the radicals

R₉₅ independently of one another are hydrogen, C₁-C₅alkyl or C₃-C₈cycloalkyl;

n₅ is a number from 5 to 12; and

R₉₈ is as defined above.

Of these, those compounds in which X and X₂ are —O— are especially important.

Particularly preferred compounds of the formula I are also those in which

R₁ is a group —NR₉₀R₉₁ or

 R₉₀ and R₉₁ independently of one another are C₁-C₁₂alkyl, C₁-C₁₂alkyl substituted by halogen, CN or C₁-C₃alkoxy, C₆-C₁₂bicycloalkyl, C₆-C₁₂bicycloalkenyl, C₃-C₁₂cycloalkyl, C₃-C₁₂cycloalkyl substituted by C₁-C₄alkyl, C₅-C₇cycloalkenyl or C₅-C₇cycloalkenyl substituted by C₁-C₄alkyl;

the radicals R₂₀ independently of one another are hydrogen or C₁-C₄alkyl;

n₁ is 1, 2, 3, 4 or 5;

n₂ is 0, 1 or 2; and

n₃ is a number from 3 to 10;

R₂ is a group R₈₈R₈₉N—;

R₈₈ and R₈₉ independently of one another are hydrogen or C₁-C₆alkyl and

in which X is —O—, —S—, —SO— or —SO₂—;

X₂ is —O—, —S— or —NR₁₀₀—;

R₁₀₀ is hydrogen or C₁-C₃alkyl;

R₂₀ is as defined above;

R₂₄ is hydrogen or methyl;

R₉₂ is hydrogen or C₁-C₄alkyl;

R₉₃ is hydrogen, C₁-C₄alkyl, C₁-C₄alkoxy or C₁-C₄alkylthio;

R₉₇ is hydrogen, halogen, NO₂, CN, C₃-C₆cycloalkoxy, C₁-C₁₀alkyl, C₁-C₁₀alkyl substituted by halogen, CN, NO₂, C₁-C₆alkoxy, C₃-C₆alkenyloxy, C₁-C₆alkoxycarbonyl or substituted or unsubstituted aryl or aryloxy, C₃-C₁₀alkenyl, C₃-C₁₀alkenyl substituted by halogen, CN, NO₂, C₁-C₆alkoxy, C₃-C₆alkenyloxy, C₁-C₆alkoxycarbonyl or substituted or unsubstituted aryl or aryloxy, C₁-C₁₀alkoxy, C₁-C₁₀alkoxy substituted by halogen, CN, NO₂, C₁-C₆alkoxy, C₃-C₆-alkenyloxy, C₁-C₆alkoxycarbonyl or substituted or unsubstituted aryl or aryloxy, C₃-C₁₀alkenyloxy, C₃-C₁₀alkenyloxy substituted by halogen, CN, NO₂, C₁-C₆alkoxy, C₃-C₆alkenyloxy, C₁-C₆alkoxycarbonyl or substituted or unsubstituted aryl or aryloxy, C₁-C₁₀alkylcarbonyl, C₁-C₁₀alkylcarbonyl substituted by halogen, CN, NO₂, C₁-C₆alkoxy, C₃-C₆alkenyloxy, C₁-C₆alkoxycarbonyl or substituted or unsubstituted aryl or aryloxy, C₁-C₁₀alkoxycarbonyl, C₁-C₁₀alkoxycarbonyl substituted by halogen, CN, NO₂, C₁-C₆alkoxy, C₃-C₆alkenyloxy, C₁-C₆alkoxycarbonyl or substituted or unsubstituted aryl or aryloxy, C₁-C₁₀alkylcarbonyloxy or C₁-C₁₀alkylcarbonyloxy substituted by halogen, CN, NO₂, C₁-C₆-alkoxy, C₃-C₆alkenyloxy, C₁-C₆alkoxycarbonyl or substituted or unsubstituted aryl or aryloxy, or R₉₇ is CHO, C₃-C₈cycloalkyl, C₁-C₄alkylthio, C₃- or C₄alkenylthio, (R₉₄)₂N—, (R₉₅)₂N—CO—, aryl, aryloxy, arylcarbonyl or aryloxycarbonyl, or a group

 the radicals R₉₄ independently of one another are hydrogen, C₁-C₁₀alkyl, C₃-C₈cycloalkyl, C₁-C₁₀alkylcarbonyl or substituted or unsubstituted arylcarbonyl;

the radicals R₉₅ independently of one another are hydrogen, C₁-C₅alkyl or C₃-C₈cycloalkyl;

n₅ is a number from 5 to 12; and

R₉₈ is hydrogen, fluorine, chlorine, bromine, CN, C₁-C₃alkoxy, C₁-C₃alkoxycarbonyl, C₁-C₃-alkoxy-C₁-C₃alkyl, C₁- or C₂halogenoalkyl, C₁-C₅alkyl, NO₂, C₃-C₅alkenyl, cyclopropyl or C₁- or C₂halogenoalkoxy.

Especially preferred compounds of these are those in which R₁ is a group

—NR₉₀R₉₁ or

 R₉₀ and R₉₁ independently of one another are C₁-C₁₂alkyl, C₁-C₁₂alkyl substituted by halogen, CN or C₁-C₃alkoxy, C₃-C₈cycloalkyl, C₃-C₈cycloalkyl substituted by methyl, C₅-C₇cycloalkenyl or C₅-C₇cycloalkenyl substituted by methyl;

the radicals R₂₀ independently of one another are hydrogen or methyl;

n₁ is 2, 3 or 4;

n₂ 0 or 1; and

n₃ is 3, 4 or 5;

R₂ is a group R₈₈R₈₉N—;

R₈₈ and R₈₉ independently of one another are hydrogen or C₁-C₃alkyl; and

in which X is —O— or —S—;

R₉₇ is hydrogen, halogen, NO₂, CN, C₁-C₁₀alkyl, C₁-C₁₀alkyl substituted by halogen, CN, NO₂, C₁-C₆alkoxy or substituted or unsubstituted aryl or aryloxy, C₃-C₁₀alkenyl, C₃-C₁₀alkenyl substituted by halogen, CN, NO₂, C₁-C₆alkoxy or substituted or unsubstituted aryl or aryloxy, C₁-C₁₀alkoxy, C₁-C₁₀alkoxy substituted by halogen, CN, NO₂, C₁-C₆alkoxy or substituted or unsubstituted aryl or aryloxy, C₃-C₁₀alkenyloxy, C₃-C₁₀alkenyloxy substituted by halogen, CN, NO₂, C₁-C₆alkoxy or substituted or unsubstituted aryl or aryloxy, C₁-C₁₀alkoxycarbonyl, C₁-C₁₀alkoxycarbonyl substituted by halogen, CN, NO₂, C₁-C₆alkoxy or substituted or unsubstituted aryl or aryloxy, C₁-C₁₀alkylcarbonyloxy or C₁-C₁₀alkylcarbonyloxy substituted by halogen, CN, NO₂, C₁-C₆alkoxy or substituted or unsubstituted aryl or aryloxy, or R₉₇ is (R₉₄)₂N—, (R₉₅)₂N—CO—, aryl, aryloxy, arylcarbonyl or aryloxycarbonyl;

the radicals R₉₄ independently of one another are hydrogen, C₁-C₄alkyl, C₃-C₈cycloalkyl, C₁-C₅alkylcarbonyl or substituted or unsubstituted arylcarbonyl; and

the radicals R₉₅ independently of one another are hydrogen, C₁-C₃alkyl or C₃-C₆cycloalkyl.

Especially preferred individual compounds from the scope of formula I are:

3-amino-5-pentafluorophenoxy-1-(trans-3,3,5-trimethylcyclohexanolyl)thiatriazine;

3-amino-5-pentafluorophenoxy-1-[(N-cis-3,3,5-trimethylcyclohexyl)methylamino]thiatriazine;

3-amino-5-pentafluorophenoxy-1-octamethyleneimino-thiatriazine;

3-amino-5-pentafluorophenoxy-1-decahydroquinolyl-thiatriazine;

3-amino-5-pentafluorophenoxy-1-tetrahydroisoquinolyl-thiatriazine; and

the compound of the formula

The compounds of the formula I can be prepared on the one hand by process steps known per se using known starting materials, and on the other hand by processes which are not known per se. The latter processes which are not known per se comprise a procedure in which, for preparation of compounds of the formula I in which R₁ is the group R₇; R₂ and R₃ independently of one another are halogen, C₁-C₁₀alkoxy, C₁-C₁₀alkoxy substituted by halogen, CN, NO₂, C₁-C₆alkoxy, C₁-C₆alkylthio, C₃-C₆alkenyloxy, C₁-C₆alkoxycarbonyl, heterocyclyl or substituted or unsubstituted aryl or aryloxy, C₃-C₁₀alkenyloxy, C₃-C₁₀alkenyloxy substituted by halogen, CN, NO₂, C₁-C₆alkoxy, C₃-C₆alkenyloxy, C₁-C₆alkoxycarbonyl or substituted or unsubstituted aryl or aryloxy, C₁-C₁₀alkylthio, C₁-C₁₀alkylthio substituted by halogen, CN, NO₂, C₁-C₆alkoxy, C₃-C₆alkenyloxy, C₁-C₆alkoxycarbonyl or substituted or unsubstituted aryl or aryloxy, C₃-C₁₀alkenylthio or C₃-C₁₀alkenylthio substituted by halogen, CN, NO₂, C₁-C₆alkoxy, C₃-C₆alkenyloxy, C₁-C₆alkoxycarbonyl or substituted or unsubstituted aryl or aryloxy, or R₂ and R₃ independently of one another are C₃-C₅alkynyloxy, C₃-C₅alkynylthio, C₃-C₈cycloalkyl-X—, C₈-C₁₂bicycloalkyl-X—, heterocyclyl-X—, alicyclyl-X—, aryl-X—, phthalidyl-X—, biphenyl-X— or heteroaryl-X—, and X is as defined under formula I,

a₁) 1,3,5-trichlorthiatriazine is used as the starting substance, and this is converted with an alcohol of the formula XVII

R₇—OH  (XVII),

 in which R₇ is as defined under formula I,

if appropriate in the presence of an equimolar amount of base and an inert organic solvent, into the compound of the formula VII

 in which R₇ is as defined,

and this compound is then either

b₁) reacted with a compound of the formula XXIII

R₁₄—X₁H  (XXIII),

 in which R₁₄ is C₁-C₁₀alkyl, C₁-C₁₀alkyl substituted by halogen, CN, NO₂, C₁-C₆alkoxy, C₁-C₆alkylthio, C₃-C₆alkenyloxy, C₁-C₆alkoxycarbonyl, heterocyclyl or substituted or unsubstituted aryl or aryloxy, C₃-C₁₀alkenyl or C₃-C₁₀alkenyl substituted by halogen, CN, NO₂, C₁-C₆alkoxy, C₃-C₆alkenyloxy, C₁-C₆alkoxycarbonyl or substituted or unsubstituted aryl or aryloxy, C₃-C₅alkynyl, C₃-C₈cycloalkyl, C₆-C₁₂bicycloalkyl, heterocyclyl or alicyclyl and X₁ is oxygen or sulfur,

in the presence of an equimolar amount of base and an inert organic solvent, or

b₂) converted with a compound of the formula XVI

R₁₂—X₁H  (XVI),

 in which R₁₂ is an aryl, phthalidyl, biphenyl or heteroaryl radical; and

X₁ is oxygen or sulfur,

in the presence of an equimolar amount of base and an aprotic solvent, into the compound of the formula VI

 in which R₃ is —X₁—R₁₂,

and this compound is either

c₂) reacted with the compound of the formula XXIII

R₁₄—X₁H  (XXIII),

 in which R₁₄ and X₁ are as defined above,

in the presence of an equimolar amount of base and an inert organic solvent, or

c₃) converted with the compound of the formula XVI

R₁₂—X₁H  (XVI),

 in which R₁₂ and X₁ are as defined above,

in the presence of an equimolar amount of base and an aprotic solvent, into the compound of the formula V

 in which R₃ is —X₁—R₁₂ and

R₇, X₁ and R₁₂ are as defined above,

and this compound is then

d₃) reacted with the compound of the formula XXIII

R₁₄—X₁H  (XXIII),

 in which R₁₄ and X₁ are as defined,

in the presence of an equimolar amount of base and in an inert organic solvent, or the compound of the formula VII

b₃) converted with 2 mol of compound of the formula XVI

R₁₂—X₁H  (XVI),

 in which R₁₂ and X₁ are as defined,

in the presence of an equimolar amount of base and in an aprotic organic solvent, into the compound of the formula V, and this compound is then reacted in a manner analogous to that described under d₃), or

a₂) 1,3,5-trichlorothiatriazine is converted with a C₆-C₁₂bicycloalkyl epoxide, a C₆-C₁₂bicycloalkyl epoxide substituted by C₁-C₃alkyl or an epoxide of the formula XVIII or XIX

 in which the radicals R₁₃ independently of one another are hydrogen, C₃-C₈alkenyl, C₁-C₁₄alkyl, C₁-C₁₄alkyl substituted by halogen, NO₂, CN, C₁-C₅alkoxy, aryloxy or C₁-C₃alkoxycarbonyl;

the radicals R₂₃ independently of one another are hydrogen or C₁-C₆alkyl;

n₈ is a number from 3-10; and

n₁₁ is 1 or 2,

in an inert organic solvent, into the compound of the formula VII in which R₇ is C₂-C₁₆-b-chloroalkyl, C₂-C₁₆-b-chloroalkyl substituted by halogen, NO₂, CN, C₁-C₅alkoxy, aryloxy or C₁-C₃alkoxycarbonyl, C₅-C₁₂-b-chlorocycloalkyl or C₅-C₁₂-b-chlorocycloalkyl substituted by C₁-C₆alkyl,

and this compound reacted further in a manner analogous to that described under b₁); b₂) and c₂); b₂), c₃) and d₃); or b₃) and d₃), or

a₃) 1,3,5-trichlorothiatriazine is reacted with an alcohol of the formula XVII

R₇—OH  (XVII),

 in which R₇ is C₁-C₁₀alkyl, C₁-C₁₀alkyl substituted by halogen, CN, NO₂, C₁-C₅alkoxy, C₁-C₅alkylthio, C₃-C₆alkenyloxy, C₁-C₃alkoxycarbonyl, heterocyclyl or substituted or unsubstituted aryl or aryloxy, C₃-C₁₀alkenyl, C₃-C₁₀alkenyl substituted by halogen, C₁-C₃alkoxy or substituted or unsubstituted aryl or aryloxy, C₃-C₅alkynyl, C₃-C₈cycloalkyl, C₆-C₁₂bicycloalkyl, heterocyclyl or alicyclyl,

if appropriate in an inert solvent in the presence of an eqimolar amount of base.

Another process according to the invention for the preparation of the compounds of the formula I in which

 R₁ is the group —OR₇;

R₂ is a group R₈₈R₈₉N—,

and R₃ is aryl-X—, phthalidyl-X—, biphenyl-X— or heteroaryl-X— comprises a procedure in which

c₄) a compound of the formula VI

 in which R₇ is as defined under formula I and

R₃ is as defined above,

is reacted with an amine of the formula XIII, XIV or XV

R₈₈R₈₉NH (XIII),

 in which R₂₀, R₈₈, R₈₉, Y and n₇ are as defined under formula I,

if appropriate in a solvent; or

c₃) the compound of the formula VI is first converted with a compound of the formula XVI

R₁₂—X₁H  (XVI),

 in which R₁₂ is an aryl, phthalidyl, biphenyl or heteroaryl radical, and

X₁ is oxygen or sulfur,

in the presence of an equimolar amount of base and in an aprotic organic solvent, into the compound of the formula V

 in which R₃ is —X₁—R₁₂ and

R₇, R₁₂ and X₁ are as defined, and

d₄) this is then reacted with an amine of the formula XIII, XIV or XV in a manner analogous to that described under C₄); or in which

a₄) 1,3,5-trichlorothiatriazine is converted with an alcoholate of the formula XVII₁

(R₇—O⁻)_(n)M₁ ^(+n)  (XVII₁),

 in which R₇ is as defined under formula I;

M₁ ^(+n) is an alkali metal or alkaline earth metal ion or a metal ion of the first or second sub-group of the Periodic Table; and

n is 1, 2, 3 or 4,

in the presence of an inert organic solvent, into the compound of the formula VII

 in which R₇ is as defined, and

b₄) this is reacted with an amine of the formula XIII, XIV or XV

R₈₈R₈₉NH

in which R₂₀, R₈₈, R₈₉, Y and n₇ are as defined under formula I,

if appropriate in a solvent, to give the compound of the formula VIII

 in which R₂ and R₇ are as defined, and

c₅) this is then reacted with a compound of the formula XVI

R₁₂—X₁H  (XVI),

 in which R₁₂ is an aryl, phthalidyl, biphenyl or heteroaryl radical; and

X₁ is oxygen or sulfur,

in a solvent in the presence of a tertiary amine and, if appropriate, another base.

The process according to the invention for the preparation of the compounds of the formula I in which

 R₁ is a group —NR₉₀R₉₁ or an N-heterocyclic radical onto which 1 or 2 further carbocyclic, heterocyclic or aromatic rings can be fused and which can contain further heteroatoms;

R₂ is a group R₈₈R₈₉N—,

 and R₃ is aryl-X—, phthalidyl-X—, biphenyl-X— or heteroaryl-X—

comprises a procedure in which

e) a compound of the formula III

 in which R₇ is as defined under formula I and

R₂ and R₃ are as defined,

is reacted with an amine of the formula XI or XII

 in which R₉₀ and R₉₁ are as defined under formula I and

R₁₁ is a cyclic radical onto which 1 or 2 further carbocyclic, heterocyclic or aromatic rings can be fused and which can contain further heteroatoms,

if appropriate in a solvent; or in which

a₅) 1,3,5-trichlorothiatriazine is converted with an amine of the formula XI or XII

 in which R₉₀ and R₉₁ are as defined under formula I and

R₁₁ is a cyclic radical onto which 1 or 2 carbocyclic, heterocyclic or aromatic rings can be fused and which can contain further heteroatoms,

or with an amide of the formula XI₁ or XII₁,

 in which R₉₀, R₉₁ and R₁₁ are as defined;

M₂ ^(+n) is an alkali metal or alkaline earth metal ion or a metal ion of the first or second sub-group of the Periodic Table; and

n is 1, 2, 3 or 4,

in the presence of an inert organic solvent and if appropriate a base, into the compound of the formula IX

 in which R₁ is as defined, and

b₅) this is reacted with an amine of the formula XIII, XIV or XV

 in which R₂₀, R₈₈, R₈₉, Y and n₇ are as defined under formula I,

if appropriate in a solvent, to give the compound of the formula X

 in which R₁ and R₂ are as defined, and

c₆) this is then reacted with a compound of the formula XVI

R₁₂—X₁H  (XVI),

 in which R₁₂ is an aryl, phthalidyl, biphenyl or heteroaryl radical; and

X₁ is oxygen or sulfur,

in a solvent in the presence of a tertiary amine and a further equivalent amount of base.

Another process according to the invention for the preparation of compounds of the formula I in which

 R₁ is a group —OR₇;

R₂ is a group R₈₈R₈₉N—,

 aryl-X—, phthalidyl-X—, biphenyl-X— or heteroaryl-X—; and R₃ is aryl-X—, phthalidyl-X—, biphenyl-X— or heteroaryl-X—, comprises a procedure in which a compound of the formula I in which

R₁ is a group —OR₇, in which

R₇ is other than in the end product; and

R₂ and R₃ are as defined

is reacted with an alcohol of the formula XVII

R₇—OH  (XVII)

 in which R₇ is other than in the starting substance of the formula I, in the presence of an inert organic solvent and a catalytic or equimolar amount of base.

The abovementioned processes according to the invention for the preparation of compounds of the formula I follow equations 1 and 2, the scope of the compounds of the formula I being composed of the scopes of the compounds of the formulae II, III and IV shown in the equations mentioned.

In equation 1 the following applies:

a₁) R₇—OH (XVII), solvent, −60°-+80° C.;

a₂) Bicycloalkyl epoxides,

 solvent, 0°-130° C.;

a₃) R₇—OH (XVII), solvent, base, for example NaH, 10°-40° C.;

b₁) R₁₄—X₁H (XXIII), solvent, base, for example NaH, −60°-+80° C.;

b₂) R₁₂—X₁H (XVI), solvent, base, for example NaH, −60°-+50° C.;

b₃) 2 mol R₁₂—X₁H (XVI), solvent, base, for example NaH, −60°-+50° C.;

c₂) R₁₄—X₁H (XXIII), solvent, base, for example K tert-butylate, −60°-+80° C.;

c₃) R₁₂—X₁H (XVI), solvent, base, for example NaH, −60°-+50° C.; and

d₃) R₁₄—X₁H (XXIII), solvent, base, for example K tert-butylate, −60°-+80° C.;

a₄) (R₇—O⁻)_(n) M₁ ^(+n) (VII₁), for example (R₇—O⁻)(MgCl)⁺, solvent, for example tetrahydrofuran, −78°-0° C.;

b₄) R₈₈R₈₉NH (XIII),

 solvent, −78°-+40° C.;

a₅) R₉₀R₉₁NH (XI) or

 base, for example Et₃N, solvent, or

(R₉₀R₉₁N⁻)_(n) M₂ ^(+n) (XI₁) or

 solvent, −78°-0° C.;

b₅) R₈₈R₈₉NH (XIII),

 solvent, −78°-+40° C.,

 in which R₇, R₁₁, R₁₂, R₁₃, R₁₄, R₂₀, R₂₃, R₈₈, R₈₉, R₉₀, R₉₁, n, n₇, n₈, n₁₁, Y, X₁, M₁ ^(+n) and M₂ ^(+n) are as defined above.

In equation 2, the following applies:

c₃) R₁₂—X₁H (XVI), solvent, base, for example NaH, −60°-+50° C.;

c₄) R₈₈R₈₉NH (XIII),

 solvent, −50°-+50° C.;

d₄) R₈₈R₈₉NH (XIII),

 solvent, −20°-+100° C.;

e) R₉₀R₉₁NH (XI) or

 solvent, 20°-150° C.;

c₅) R₁₂—X₁H (XVI), solvent, tertiary amine, for example (CH₃)₃N, if appropriate base, for example NaOH, −10°-+70° C.;

c₆) R₁₂—X₁H (XVI), solvent, tertiary amine, for example (CH₃)₃N, base, for example NaOH, −10°-+70° C.;

p) R₇—OH (XVII), solvent, base_(cat), for example NaH, −60°-+50° C.; and

q) R₇—OH (XVII), solvent, base, for example NaH, 0°-+50° C.;

 in which R₇, R₁₁, R₁₂, R₂₀, R₈₈, R₈₉, R₉₀, R₉₁, Y, n₇ and X₁ are as defined above.

The substitution of the most reactive chlorine atom on the sulfur of the 1,3,5-trichloro-thiatriazine leads on the one hand by a process variant a₁), by reaction with the alcohol of the formula XVII, by process variant a₂), by reaction with bicycloalkyl epoxides or epoxides of the formula XVIII or XIX, or by process variant a₄), by reaction with alcoholates of the formula XVII₁, to the compounds of the formula VII, and on the other hand by process variant a₃), by reaction with the alcohol of the formula XVII, directly to the compounds of the formula IV (equation 1).

Process variant a₂) always gives 1-b-chloroalkoxy derivatives of the formula VII here.

The reaction according to process variant a₁) is advantageously carried out in a non-polar organic solvent which is inert in the reaction, such as chlorinated hydrocarbons, for example methylene chloride, chloroform or carbon tetrachloride, aromatic hydrocarbons, for example benzene, toluene or xylenes, cyclic hydrocarbons, for example cyclohexane, or cyclic ethers, for example tetrahydrofuran or dioxane, at reaction temperatures of −60° C. to +80° C., preferably at temperatures of −30° C. to +50° C., if appropriate in the presence of an equimolar amount of base. Examples of suitable bases are organic bases, such as tertiary amines, for example trimethylamine, triethylamine, quinuclidine, 1,4-diazabicyclo-[2.2.2]octane, 1,5-diazabicyclo[4.3.0]non-5-ene or 1,5-diazabicyclo[5.4.0]undec-7-ene or alcoholates, for example potassium tert-butylate, sodium methylate or sodium ethylate. However, inorganic bases, such as hydrides, for example sodium or calcium hydride, hydroxides, such as sodium or potassium hydroxide, carbonates, such as sodium or potassium carbonate, or bicarbonates, such as potassium or sodium bicarbonate, can also be used as bases. In a preferred embodiment (Example H2), 2-chloroethanol and an equimolar amount of triethylamine are dissolved in carbon tetrachloride and a solution of 1,3,5-trichlorothiatriazine in carbon tetrachloride is added to this cooled solution (−15° C.), and the mixture is subsequently warmed to 0° C.

The reaction of 1,3,5-trichlorothiatriazine with bicycloalkyl epoxides or with epoxides of the formula XVIII or XIX is expediently carried out in the same solvents as listed under variant a₁) at reaction temperatures of 0° to 130° C., preferably at reaction temperatures of 25° to 80° C.

In a preferred embodiment (Example H1), 1,3,5-trichlorothiatriazine is dissolved in carbon tetrachloride and an equimolar amount of cyclohexene oxide is added at room temperature.

In process variant a₄), 1,3,5-trichlorothiatriazine is reacted with an alcoholate of the formula XVII₁

(R₇—O⁻)_(n) M₁ ^(+n)  (XVII₁),

in which R₇ is as defined under formula I;

M₁ ^(+n) is a mono- or polyvalent metal ion, for example an alkali metal or alkaline earth metal ion or a metal ion of the first or second sub-group of the Periodic Table, preferably lithium, magnesium, zinc, aluminium, silicon, fin or titanium, but especially preferably magnesium; and n is the number 1, 2, 3 or 4 (=oxidation number of the corresponding metal ion) in the presence of an inert organic solvent, such as ethers, for example diethyl ether or tetrahydrofuran (THF).

In the compounds of the formula XVII₁ in the case of polyvalent metal ions M₁ ^(+n), if n>1, further substituents, for example halogen, C₁-C₄alkyl or cyano, are also possible in addition to one or more R₇—O⁻ groups. Furthermore, the alcoholates of the formula XVII₁ can also be employed in combination With salts, for example aluminium, tin or zinc chloride or aluminium or zinc bromide.

The reaction temperatures for this reaction range from −70° to +20° C., but are preferably below 0° C.

The resulting compound of the formula VII can be isolated, if appropriate, or else used directly for the next reaction stage.

In process variant a₃), the most reactive chlorine atom on the sulfur of the thiatriazine ring is replaced in particular by the group —OR₇ with addition of an equimolar amount of base; the less reactive chlorine atoms on the carbon atoms in the 3- and 5-positions can also be partly or completely replaced by the group —OR₇, depending on the reaction conditions (for example low reaction temperatures; slow warming of the reaction mixture).

The replacement according to variant a₃) is advantageously carried out in the presence of a non-polar organic solvent which is inert in the reaction. Such solvents are listed under variants a₁) and a₂). The alcohol of the formula XVII is accordingly converted into the corresponding alcoholate in the solvent by treatment with a strong base, such as metal hydrides, for example sodium hydride, and this alcoholate solution is added dropwise to a solution of 1,3,5-trichlorothiatriazine at temperatures of 10° to 40° C., in particular at temperatures of 20° to 30° C., while cooling.

In a preferred embodiment (Example H9), the 1,3,5-trichlorothiatriazine is dissolved in tetrahydrofuran and a methanolic sodium methylate solution in tetrahydrofuran is added dropwise at 30° C., while cooling. Completely substituted 1,3,5-trimethoxythiatriazine is obtained.

Preparation of the thiatriazine derivatives of the formula VI (equation 1) according to process variant b₂) is advantageously carried out by reaction of the corresponding 3,5-dichloro-thiatriazine of the formula VII with an alcohol of the formula XVI

R₁₂—X₁H  (XVI),

in which R₁₂ and X₁ are as defined,

in the presence of an organic solvent which is inert in the reaction, such as cyclic ethers, for example tetrahydrofuran or dioxane, and an equimolar amount of base, for example alkali metal hydrides, preferably sodium or lithium hydride, or alcoholates, for example potassium tert-butylate. The reaction temperatures range from −60° to +50° C., preferably from +40° to −10° C.

In a preferred embodiment (Example H4), ethyl salicylate is dissolved in tetrahydrofuran together with the equimolar amount of sodium hydride, 1-chloroethoxy-3,5-dichlorothiatriazine is added dropwise at −30° C. and the mixture is then warmed to room temperature.

The substitution of the remaining chlorine atom in the thiatriazine derivative of the formula VI with a further radical —X₁R₁₂ is carried out in accordance with process variant c₃). This reaction advantageously proceeds analogously to variant b₂), and leads to symmetrically or asymmetrically substituted thiatriazine derivatives of the formula V, depending on the compound of the formula XVI employed (equation 1).

The thiatriazine derivatives of the formula V can also be prepared directly from the compounds of the formula VII according to process variant b₃), and leads exclusively to symmetrically substituted derivatives being formed. The reaction according to process variant b₃) is advantageously carried out analogously to process variant b₂) or c₃), but with the difference that two molar equivalents of the compound of the formula XVI and accordingly two molar equivalents of base are employed.

The preparation of the thiatriazine derivatives of the formula IV (equation 1), in which R₂, R₃ and R₇ are as defined,

is advantageously carried out in accordance with process variant d₃) from the thiatriazine derivatives of the formula V by reaction with alcohols or thiols of the formula XXIII

R₁₄—X₁H  (XXIII),

in which R₁₄ and X₁ are as defined,

in an inert organic solvent analogously to process variant a₁) at temperatures of −60° to +80° C., preferably −50° C. to room temperature, in the presence of an equimolar amount of base. Suitable bases are, for example, organic bases, such as tertiary amines, for example triethylamine, alcoholates, for example potassium tert-butylate, or inorganic bases, such as alkali metal hydrides, for example sodium or lithium hydride. If appropriate, the alcohol of the formula XXIII can also be used as the solvent. Partial or complete exchange can take place both on the sulfur atom (1-position) and on the carbon atoms in the 3- and 5-positions, depending on the reaction conditions (reaction temperature, reaction time) and the ease of substitution of the substituents in the starting compound of the formula V. In a preferred embodiment (Example H10), 1-(b-chloroethoxy)-3,5-di(2′,5′-difluorophenoxy)-thiatriazine is dissolved in methanol and a sodium methylate solution in methanol is added dropwise at low temperatures (−60° C.). The derivative substituted by methoxy in the 1-position is first formed by this procedure and is converted into 1,3-dimethoxy-5-(2′,5′-di-fluorophenoxy)thiatriazine when the reaction solution is warmed.

In another preferred embodiment (Example H11), 1-(b-chloroethoxy)-3,5-di(2′,4′-dichlorophenoxy)thiatriazine is dissolved in tetrahydrofuran and a solution of 2,2,2-trichloroethanol and sodium hydride is added dropwise at low temperatures (−50° C.). After the reaction mixture has been warmed up, the derivative of the formula IV substituted by 2,2,2-trichloroethoxy in the 3- and 5-positions on the thiatriazine ring is isolated.

The reactions according to process variants b₁) and c₂) (equation 1) starting from the thiatriazine intermediates of the formulae VII and VI also give thiatriazines of the formula IV. Both variants b₁) and c₂) are advantageously carried out analogously to process variant d₃) by reaction of the thiatriazine intermediates of the formula VII or VI with alcohols or thiols of the formula XXIII in organic solvents which are inert in the reaction at reaction temperatures of −60° to +80° C.

In these two process variants b₁) and c₂) also, partial or complete exchange of the substituents in the 1-, 3- and 5-positions can be obtained, depending on the reactivity of the substituents in the 1-, 3- and 5-positions of the thiatriazine intermediates of the formulae VII and VI and on the reaction conditions, for example the use of an equimolar amount of alcohol or thiol of the formula XXIII and an equimolar or catalytic amount of base.

In an embodiment preferred for variant b₁) (Example H12), 1-(b-chloroethoxy)-3,5-di-chlorothiatriazine is dissolved in tetrahydrofuran and a solution of 3 molar equivalents of tert-butylmercaptan and triethylamine in tetrahydrofuran is added dropwise at low temperatures (−50° C.). After the reaction mixture has been warmed up to 0° C., a 4/1 product mixture comprising 1-(b-chloroethoxy)-3-chloro-5-tert-butylmercaptothiatriazine and 1-(b-chloroethoxy)-3,5-di-tert-butylmercaptothiatriazine is obtained.

The preparation of the thiatriazine derivatives of the formula VIII (equation 1) according to process variant b₄) is advantageously carried out by reaction of the 3,5-dichlorothiatriazine of the formula VII with an amine of the formula XIII, XIV or XV, if appropriate in the presence of a solvent, preferably tetrahydrofuran or acetonitrile, if appropriate mixed with water, at reaction temperatures of −78° to +40° C.

In a preferred embodiment (Example H20), 3,5-dichloro-1-(3-hexyloxy)thiatriazine is reacted with ammonia in tetrahydrofuran at 0° C.

In process variant a₅) in equation 1, the most reactive chlorine atom on the sulfur atom of the trichlorothiatriazine is substituted by addition of an amine of the formula XI or XII in an inert organic solvent and if appropriate in the presence of a base, for example a tertiary amine, for example triethylamine. Suitable solvents for this substitution are ethers, for example tetrahydrofuran, at reaction temperatures of −78° to +25° C., but preferably at reaction temperatures below −40° C.

Alternatively, instead of the amines of the formula XI or XII, the amides of the formula XI₁ or XII₁

(R₉₀R₉₁N⁻)_(n) M₂ ^(+n) (XI₁) or

 in which R₉₀ and R₉₁ are as defined under formula I;

R₁₁ is a cyclic radical onto which 1 or 2 carbocyclic, heterocyclic or aromatic rings can be fused and which can contain further heteroatoms;

M₂ ^(+n) is an alkali metal or alkaline earth metal ion or a metal ion of the first or second sub-group of the Periodic Table; and

n is the number 1, 2, 3 or 4 (=oxidation number of the corresponding metal ion), can be reacted with the 1,3,5-trichlorothiatriazine in an organic solvent, for example an ether, for example diethyl ether or, preferably tetrahydrofuran.

The reaction temperatures range from −78° to 0° C., but are preferably below −40° C. In the compounds of the formula XI₁ or XII₁, in the case of polyvalent metal ions M₂ ^(+n if n>)1, further substituents, for example halogen or C₁-C₄alkyl, are also possible in addition to one or more amide groups.

The compound of the formula IX can be isolated, if appropriate, or else used directly for the next reaction stage (b₅)).

In a preferred embodiment (Example H21), a mixture comprising equimolar amounts of octahydroindole and triethylamine is added dropwise to 1,3,5-trichlorothiatriazine in diethyl ether at −70° to −60° C.

Further reaction of the thiatriazine of the formula IX in accordance with process variant b₅) in equation 1 gives the thiatriazine of the formula X. This process variant is advantageously carried out analogously to process variant b₄).

In a preferred embodiment (Example H23), an aqueous ammonia solution is added to 3,5-dichloro-1-(octahydroindol-1-yl)thiatriazine in tetrahydrofuran.

In another preferred embodiment (Example H22), a suspension of piperidine and n-butyllithium is added dropwise to a solution of trichlorothiatriazine in tetrahydrofuran which has been cooled to −60° C., and the mixture is subsequently treated further with ammonia gas at −10° C. until the conversion is complete.

In the reactions according to process variants p) and q) (equation 2), only the substituent in the 1-position, i.e. on the sulfur atom of the thiatriazine ring, is substituted selectively.

The thiatriazine derivatives of the formula III can be obtained either by reaction of the 3-chlorothiatriazine derivatives of the formula VI with the amines of the formula XIII, XIV or XV in accordance with process variant c₄), or by reaction of the 5-chlorothiatriazine derivatives of the formula VIII with an alcohol of the formula XVI in accordance with process variant c₅) (equation 2).

The substitution reaction according to variant c₄) can advantageously be carried out in an inert organic solvent, such as a cyclic ether, for example tetrahydrofuran or dioxane, at temperatures of −50° to +50° C., preferably at temperatures of −20° to +20° C.

In a preferred embodiment (Example H15), 3-chloro-1-(b-chloroethoxy)-5-(2′-carboethoxyphenoxy)thiatriazine is dissolved in tetrahydrofuran, and dimethylamine is passed in at 0° C. until conversion is complete.

The substitution reaction according to variant c₅) can advantageously be carried out in an organic solvent, such as an ether, for example tetrahydrofuran, or a halogenated hydrocarbon, for example methylene chloride, to which water is admixed, if appropriate, in the presence of a catalytic to excess amount of a tertiary amine, for example trimethylamine, and in the presence or absence of a further base, for example sodium hydroxide, at temperatures from −10° to +70° C., preferably at 0° to 25° C.

In a preferred embodiment (Example H16), a mixture of 3-amino-5-chloro-1-(3-hexyloxy)thiatriazine, difluorophenol and trimethylamine in methylene chloride is allowed to react at 20° C.

Another possibility for the preparation of the thiatriazines of the formula III starts from the thiatriazine intermediates of the formula V, one of the radicals —X₁R₁₂ being substituted by amines of the formula XIII, XIV or XV according to process variant d₄) (equation 2). This substitution reaction is advantageously carried out analogously to variant c₄) in an inert organic solvent at temperatures from −20° to +100° C., preferably at 0° to 50° C.

According to process variant e), in equation 2, the group —OR₇ bonded to the sulfur of the thiatriazine ring of the formula III can be substituted selectively by an amino group. As a result, compounds of the formula II in which

R₁ is a group —NR₉₀R₉₁ or an N-heterocyclic radical, are obtained. This reaction is advantageously carried out with amines of the formula XI or XII in an inert organic solvent, such as an aromatic hydrocarbon, for example toluene or xylenes, at temperatures of 20° to 150° C., preferably at temperatures of 50° to 100° C.

In a preferred embodiment (Example H18), 1-(2′-chlorocyclohexanolyl)-3-amino-5-(2′,6′-difluorophenoxy)thiatriazine is heated at 80°-90° C. together with decahydroquinoline in toluene until conversion is complete.

Another possibility for the preparation of the thiatriazines of the formula II starts from the 1,3-disubstituted 5-chlorothiatriazines of the formula X, the 5-chlorine atom being replaced by alcohols of the formula XVI according to process variant c₆) in equation 2. This replacement is advantageously carried out in the presence of a catalytic to excess amount of a tertiary amine, for example trimethylamine, and a further equivalent amount of base, for example sodium hydroxide, in an organic solvent, such as an ether, for example tetrahydrofuran, or a halogenated hydrocarbon, for example methylene chloride, to which water is admixed if appropriate. The reaction temperatures are −10° to +70° C., preferably 0° to 25° C.

In a preferred embodiment (Example H19), 3-amino-5-chloro-1-(piperidin-1-yl)thiatriazine and pentafluorophenol are brought together in methylene chloride with 2N sodium hydroxide solution and aqueous trimethylamine and allowed to react. In the thiatriazine derivatives of the formulae V and III, the group —OR₇ bonded to the sulfur can be substituted selectively by another alcohol of the formula XVII

R₇—OH  (XVII),

in which R₇ is as defined under formula I, according to process variants p) and q) in equation 2.

Other compounds of the formulae V and III and of the formula I can be prepared in this way and by customary derivatzation.

In the case of the compounds of the formula V, this exchange is advantageously carried out according to process variant p) with an excess of alcohol, but at least the equimolar amount of alcohol, in an inert organic solvent, such as a cyclic ether, for example tetrahydrofuran or dioxane, at temperatures from −60° to +50° C., preferably at temperatures from −40° to +10° C., in the presence of a catalytic amount of base, for example 1-30 mol %, preferably 5-20 mol %. Suitable bases are, for example, metal hydrides, such as sodium hydride, or alcoholates, such as potassium tert-butylate.

The exchange of the group —OR₇ in the case of the compounds of the formula III in accordance with process variant q) can be carried out analogously to process variant p), with the difference that reaction temperatures of 0° to 50° C., preferably 10° to 30° C., are used and that the amount of base used for the exchange reaction is less critical. Equimolar amounts of bases are preferably used.

In a preferred embodiment (Example H14), isopropanol and sodium hydride are initially introduced into tetrahydrofuran and 3-amino-1-(b-chloroethoxy)-5-(2′,5′-difluorophenoxy)thiatriazine is added to this suspension at room temperature.

The thiatriazines of the formula I or of the formulae II, III and IV, in which

R₂ and/or R₃ is aryl-X—, phthalidyl-X—, biphenyl-X— or heteroaryl-X—; and

X is sulfur,

obtained in the process variants described above can subsequently be oxidized to give the corresponding sulfoxides and sulfone derivatives of the formula I or of the formulae II, III and IV, in which

R₂ and/or R₃ is aryl-X—, phthalidyl-X—, biphenyl-X— or heteroaryl-X—; and

X is —SO— or —SO₂—,

analogously to known standard processes, for example with hydrogen peroxide or m-chloroperbenzoic acid. In order to avoid undesirable side reactions, the conditions for this oxidation must be evaluated in respect of the reactivities of the other substituents on the thiatriazine ring. Examples of such sulfur oxidations are described in Houben-Weyl, “Methoden der Organischen Chemie” [Methods of Organic Chemistry], Fourth edition, Volume IV, Georg Thieme Verlag Stuttgart.

The present processes according to the invention have the following advantages:

1. Easy accessibility of the 1,3,5-trichlorothiatriazine and of the other starting compounds of the formulae XVII, XVIII, XIX, XVI, XXIII, XI, XII, XIII, XIV and XV, and of the bicycloalkyl epoxides from the scope of formula I;

2. Low number of synthesis stages;

3. Selectivity of the exchange reactions on the thiatriazine ring;

4. Wide possibilities for derivatization in respect of the choice of substituents R₁, R₂ and R₃ on the thiatriazine ring and associated wide possibilities of variation for the thiatriazines of the formula I; and

5. Exchange reactions are carried out under mild reaction conditions (for example low temperatures) and are compatible for a large number of functional groups.

The thiatriazine derivatives of the formulae V, VI, VII, VII, IX and X are novel. They are important intermediates for the synthesis of the compounds of the formula 1. The invention therefore also relates to these novel compounds and processes for their preparation, and to the use of the compounds of the formulae V, VI, VII, VIII, IX and X for the preparation of compounds of the formula I, excluding the compounds

wherein R₀₁ is hydrogen, methyl, ethyl, n-propyl, i-butyl or cyclohexyl; and R₀₂ and R₀₃ are ethyl or benzyl.

For the intermediates of the formulae V, VI, VII, VIII, IX and X, the same preferences apply in respect of R₃ and R₇ as for the compounds of the formula I.

The starting compounds of the formulae XVII, XVIII and XIX required in process variants a₁), a₂), a₃), p) and q) and the corresponding bicycloalkyl epoxides from the scope of formula I either are obtainable commercially or can be prepared by generally known methods. The preparation of such compounds is described, for example, in Houben-Weyl, “Methoden der Organischen Chemie” [Methods of Organic Chemistry], Fourth edition, Volume VI and VI/3, Georg Thieme Verlag Stuttgart.

The starting compounds of the formulae XVI and XXIII required in process variants b₁), b₂), b₃), c₂), c₃) and d₃) either are obtainable commercially or can be prepared by generally known methods. The preparation of such compounds is described, for example, in Houben-Weyl, “Methoden der Organischen Chemie” [Methods of Organic Chemistry], Fourth edition, Volume VI and IX, Georg Thieme Verlag Stuttgart.

The amines of the formulae XI, XII, XIII, XIV and XV required in process variants c₄), d₄) and e) either are obtainable commercially or can be prepared analogously to known standard processes. The preparation of such compounds is described, for example, in Houben-Weyl, “Methoden der Organischen Chemie” [Methods of Organic Chemistry], Fourth edition, Volume XI, Georg Thieme Verlag Stuttgart.

The alcoholates of the formula XVII₁ required in process variant a₄) can be prepared analogously to known standard processes, for example by reaction of the corresponding alcohol of the formula XVII with an M₁-organometallic compound, for example C₁-C₄alkyllithium or C₁-C₈alkylmagnesium halide, or by reaction with an M₁-metal compound which contains at least one leaving group, for example cyano or, preferably, halogen, and if appropriate one or more C₁-C₄alkyl groups, in the presence of a base. The compounds of the formula XVII₁ do not have to be isolated in a pure form, but can be further used directly.

The amides of the formulae XI₁ and XII₁ required in process variant a₅) can be prepared analogously to known standard processes, for example by reaction of the corresponding amines of the formula XI and XII with an M₂-organometallic compound, for example C₁-C₄alkyllithium or C₁-C₈alkylmagnesium halide, or by reaction with an M₂-metal compound which has at least one leaving group, for example halogen, and where appropriate one or more C₁-C₄alkyl groups, in the presence of a base.

The preparation of the starting compound 1,3,5-trichlorothiatriazine is described in DD-A-113 006 (Example 1).

The resulting compounds of the formula I can be isolated in the customary manner by concentration or evaporation of the solvent, and purified by recrystallization or trituraaon of the solid residue in solvents in which they do not dissolve readily, such as ethers or aliphatic hydrocarbons, by distillation or by means of column chromatography with a suitable eluting agent.

If no controlled synthesis is carried out for isolation of pure isomers or diastereomers, the product can be obtained as a mixture of two or more isomers or diastereomers. The isomers or diastereomers can be separated by methods known per se. If desired, for example, pure optically active isomers or diastereomers can also be prepared by synthesis from corresponding optically active starting materials, for example cis- or trans-decalin, cis- or trans-2,6-dimethylmorpholine or cis- or trans-decahydro(iso)quinoline.

The end products of the formula I can be isolated in the customary manner by concentration and/or evaporation of the solvent and purified by recrystallization or trituration of the solid residue in solvents in which they do not dissolve readily, such as ethers, aromatic hydrocarbons or chlorinated hydrocarbons.

For use according to the invention of the compounds of the formula I, including the compounds of the formulae I₁ to I₇, or compositions comprising these, all the methods of application customary in agriculture, for example preemergence and postemergence application, as well as various methods and techniques such as, for example, controlled release of the active compound, are suitable. For this, the active compound is adsorbed in solution onto mineral granule carriers or polymerized granules (urea/formaldehyde) and the granules are dried. If appropriate, a coating can additionally be applied (coated granules), allowing the active compound to be released in a metered form over a certain period of time.

The compounds of the formula I, including the compounds of the formulae I₁ to I₇, can be employed in unchanged form, i.e. as they are obtained in the synthesis, but they are preferably processed in the customary manner with the auxiliaries customary in formulation technology, for example to give emulsifiable concentrates, solutions which can be sprayed or diluted directly, dilute emulsions, wettable powders, soluble powders, dusts, granules or microcapsules. The methods of application, such as spraying, atomizing, dusting, wetting, scattering or pouring, like the nature of the compositions, are chosen according to the required aims and the given circumstances.

The formulations, i.e. the compositions, formulations, preparations, combinations or mixtures comprising the active compound of the formula I or at least one active compound of the formula I, including the compounds of the formulae I₁ to I₇ and as a rule one or more solid or liquid formulation auxiliaries, are prepared in a known manner, for example by intimate mixing and/or grinding of the active compounds with the formulation auxiliaries, for example solvents or solid carriers. Surface-active compounds (surfactants) can, furthermore, additionally be used in the preparation of the formulations.

Solvents can be: aromatic hydrocarbons, preferably fractions C₈ to C₁₂, for example xylene mixtures or substituted naphthalenes phthalic acid esters, such as dibutyl or dioctylphthalate, aliphatic hydrocarbons, such as cyclohexane or paraffins, alcohols and glycols, and ethers and esters thereof, such as ethanol, ethylene glycol or ethylene glycol monomethyl or -ethyl ether, ketones, such as cyclohexanone, strongly polar solvents, such as N-methyl-2-pyrrolidone, dimethyl sulfoxide or N,N-dimethylformamide, and epoxidized or non-epoxidized vegetable oils, such as epoxidized coconut oil or soya oil; or water.

Solid carriers, for example for dusts and dispersable powders, which are used are as a rule natural rock powders, such as calcite, talc, kaolin, montmorillonite or attapulgite. Highly disperse silicic acid or highly disperse absorbent polymers can also be added to improve the physical properties of the formulation. Granular adsorptive carriers for granules are porous types, for example pumice, crushed brick, sepiolite or bentonite, and non-sorbent carrier materials are, for example, calcite or sand. A large number of pregranulated materials of inorganic or organic nature, such as, in particular, dolomite or comminuted plant residues, can moreover be used.

Surface-active compounds are nonionic, cationic and/or anionic surfactants and surfactant mixtures having good emulsifying, dispersing and wetting properties, depending on the nature of the active compound of the formula I to be formulated

Suitable anionic surfactants can be both so-called water-soluble soaps and water-soluble synthetic surface-active compounds.

Soaps are the alkali metal, alkaline earth metal or substituted or unsubstituted ammonium salts of higher fatty acids (C₁₀-C₂₂), for example the Na or K salts of oleic or stearic acid, or of naturally occurring fatty acid mixtures, which can be obtained, for example, from coconut oil or tallow oil. They are also the fatty acid methyl-taurine salts.

However, so-called synthetic surfactants are more frequently used, in particular fatty alcohol sulfonates, fatty alcohol sulfates, sulfonated benzimidazole derivatives or alkylarylsulfonates.

The fatty alcohol sulfonates or sulfates are as a rule in the form of alkali metal, alkaline earth metal or substituted or unsubstituted ammonium salts and contain an alkyl radical having 8 to 22 C atoms, alkyl also including the alkyl moiety of acyl radicals, for example the Na or Ca salt of ligninsulfonic acid, of dodecyl-sulfuric acid ester or of a fatty alcohol sulfate mixture prepared from naturally occurring fatty acids. These also include the salts of the sulfuric acid esters and sulfonic acids of fatty alcohol-ethylene oxide adducts. The sulfonated benzimidazole derivatives preferably contain 2 sulfonic acid groups and a fatty acid radical having 8-22 C atoms. Alkylarylsulfonates are, for example, the Na, Ca or triethanolamine salts of dodecylbenzenesulfonic acid, of dibutyinaphthalenesulfonic acid or of a naphthalenesulfonic acid-formaldehyde condensation product.

Salts can furthermore also be corresponding phosphates, for example salts of the phosphoric acid ester of a p-nonylphenol-(4-14)-ethylene oxide adduct, or phospholipids.

Nonionic surfactants are, in particular, polyglycol ether derivatives of aliphatic or cycloaliphatic alcohols, saturated or unsaturated fatty acids and alkylphenols, which can contain 3 to 30 glycol ether groups and 8 to 20 carbon atoms in the (aliphatic) hydrocarbon radical and 6 to 18 carbon atoms in the alkyl radical of the alkylphenols.

Other suitable nonionic surfactants are the water-soluble adducts, containing 20 to 250 ethylene glycol ether groups and 10 to 100 propylene glycol ether groups, of polyethylene oxide on polypropylene glycol, ethylenediaminopolypropylene glycol and alkylpolypropylene glycol having 1 to 10 carbon atoms in the alkyl chain. The compounds mentioned usually contain 1 to 5 ethylene glycol units per propylene glycol unit.

Examples of nonionic surfactants are nonylphenolpolyethoxyethanols, castor oil polyglycol ether, polypropylene-polyethylene oxide adducts, tributylphenoxypolyethoxyethanol, polyethylene glycol and octylphenoxypolyethoxyethanol.

Fatty acid esters of polyoxyethylene sorbitan, such as polyoxyethylene sorbitan trioleate, can also be used.

The cationic surfactants are, in particular, quaternary ammonium salts, which contain at least one alkyl radical having 8 to 22 C atoms as N substituents and lower, halogenated or non-halogenated alkyl, benzyl) or lower hydroxyalkyl radicals as further substituents. The salts are preferably in the form of halides, methyl sulfates or ethyl sulfates, for example stearyltrimethylammonium chloride or benzyldi(2-chloroethyl)ethyl ammonium bromide.

The surfactants customary in formulation technology which can also be used in the compositions according to the invention are described, inter alia, in “Mc Cutcheon's Detergents and Emulsifiers Annual”, MC Publishing Corp., Ridgewood N.J., 1981, Stache, H., “Tensid-Taschenbuch” [Surfactant Handbook], Carl Hanser Verlag, Munich/Vienna, 1981 and M. and J. Ash, “Encyclopedia of Surfactants”, Volume I-III, Chemical Publishing Co., New York, 1980-81.

The herbicidal formulations as a rule comprise 0.1 to 99% by weight, in particular 0.1 to 95% by weight, of herbicide, 1 to 99.9% by weight, in particular 5 to 99.8% by weight, of a solid or liquid formulation auxiliary and 0 to 25% by weight, in particular 0.1 to 25% by weight, of a surfactant.

While concentrated compositions are more preferable as commercial goods, the end user as a rule uses dilute compositions.

The compositions can also comprise further additives, such as stabilizers, for example epoxidized or nonepoxidized vegetable oils (epoxidized coconut oil, rapeseed oil or soya oil), defoamers, for example silicone oil, preservatives, viscosity regulators, binders, tackifiers and fertilizers or other active compounds.

In particular, preferred formulations have the following composition:

(%=per cent by weight)

Emulsifiable Concentrates:

Active compound: 1 to 90%, preferably 5 to 50%

Surface-active agent: 5 to 30%, preferably 10 to 20%

Solvent: 15 to 94%, preferably 70 to 85%

Dusts:

Active compound: 0.1 to 50%, preferably 0.1 to 1%

Solid carrier: 99.9 to 90%, preferably 99.9 to 99%

Suspension Concentrates:

Active compound: 5 to 75%, preferably 10 to 50%

Water: 94 to 24%, preferably 88 to 30%

Surface-active agent: 1 to 40%, preferably 2 to 30%

Wettable Powders:

Active compound: 0.5 to 90%, preferably 1 to 80%

Surface-active agent: 0.5 to 20%, preferably 1 to 15%

Solid carrier material: 5 to 95%, preferably 15 to 90%

Granules:

Active compound: 0.1 to 30%, preferably 0.1 to 15%.

Solid carrier: 99.5 to 70%, preferably 97 to 85%

The active compounds of the formula I, including the compounds of the formulae I₁ to I₇, are as a rule successfully employed on the plants or their environment with rates of application of 0.001 to 4 kg/ha, in particular 0.005 to 2 kg/ha. The dosage required for the desired action can be determined by experiments. It depends on the mode of action, the stage of development of the crop plant and the weed and on the application (location, time, method), and can vary within relatively wide limits as a result of these parameters.

The compounds of the formula I, including the compounds of the formulae I₁ to I₇, have herbicidal and growth-inhibiting properties which enable them to be used in crops of useful plants, in particular in cereals, cotton, soya, sugar beet, sugar cane, plantation crops, oilseed rape, maize and rice.

Crops are also to be understood as those which have been rendered tolerant to herbicides or classes of herbicide by conventional breeding or genetic engineering methods.

The weeds to be controlled can be both monocotyledon and dicotyledon weeds, for example Stellaria, Nasturtium, Agrostis, Digitaria, Avena, Setaria, Sinapis, Lolium, Solanum, Phaseolus, Echinochloa, Scirpus, Monochoria, Sagittaria, Bromus, Alopecurus, Sorghum halepense, Rottboellia, Cyperus, Abutilon, Sida, Xanthium, Amaranthus, Chenopodium, lpomoea, Chrysanthemum, Galium, Viola and Veronica.

The following examples illustrate the invention further, without limiting it.

PREPARATION EXAMPLES Example H1 Preparation of 1-(trans-2-chlorocyclohexyloxy)-3,5-dichlorothiatriazine (process a₂)

5.11 g (0.025 mol) of 1,3,5-trichlorothiatriazine are dissolved in 50 ml of carbon tetrachloride, and 2.94 g (0.03 mol) of cyclohexene oxide are added at 25° C. The weakly exothermic reaction is carried out at 25-35° C. and has ended after 30 minutes. The cloudy solution formed is filtered and the filtrate is concentrated. 8.7 g of crude product are obtained as a residue, recrystallization of which from a mixture of ethyl acetate and hexane gives 6.75 g (89% of theory) of the desired product of melting point 82-83° C.

Example H2 Preparation of 1-(2-chloroethoxy)-3,5-dichlorothiatriazine (process a₁)

0.80 g (0.01 mol) of 2-chloroethanol and 1.21 g (0.012 mol) of triethylamine are dissolved in 30 ml of carbon tetrachloride and the solution is cooled to −15° C. Thereafter, a solution of 2.04 g (0.01 mol) of 1,3,5-trichlorothiatriazine in 5 ml of carbon tetrachloride is added dropwise at this temperature and the temperature is then allowed to rise to 0° C. The triethylamine hydrochloride is filtered off and the filtrate is concentrated to give 1.85 g of crude product. Recrystallization from 10 ml of hexane gives 1.65 g (67% of theory) of the desired product of melting point 54-55° C.

Example H3 Preparation of 1-methoxy-3,5-dichlorothiatriazine (process a₁)

4.09 g (0.02 mol) of 1,3,5-trichlorothiatriazine are stirred as a suspension in 50 ml of carbon tetrachloride at −25° C., and a solution of 0.70 g (0.022 mol) of methanol in a little carbon tetrachloride is added dropwise. During this operation, the trichlorothiatriazine dissolves apart from a little insoluble product. The mixture is then warmed to 0° C. and filtered and the filtrate is concentrated on a rotary evaporator at a maximum of 50° C. 3.25 g of the desired product, which, according to the ¹³C-NMR spectrum and thin layer chromatogram (silica gel; eluting agent ethyl acetate/hexane 1/3), contains practically no further impurities, are obtained as the residue. The compound is unstable and decomposes within a few hours when left to stand.

The compounds listed in the following Table I can be prepared analogously to Examples H1 to H3.

TABLE 1 Compounds of the formula VII (VII)

Comp. No. R₇ Process Physical data 1.1 —CH₃ a₁ ¹³C-NMR: 167.5 ppm; 52.6 ppm 1.2 —C₂H₅ 1.3 —C₅H₁₁(n) 1.4 —C₁₀H₂₁(n) 1.5 —CH(CH₃)₂ 1.6 —CH₂CH(CH₃)₂ 1.7 —CH₂CH₂Cl a₁ Melting point 54-55° C. 1.8 —CH₂CHBrCH₂Br 1.9 —CH₂CH₂F 1.10 —CH₂CH₂(CF₂)₃CF₃ 1.11

1.12 —CH₂CHCl₂ a₁ ¹³C-NMR: 167.7 ppm; 71.1 ppm; 68.6 ppm 1.13 —CH(CH₃)(CH₂)₅CH₃ 1.14

1.15

a₂ Melting point 82-83° C. 1.16

1.17

1.18

1.19

a₂ ¹³C-NMR: 166.8 ppm; 88.9 ppm; 64.5 ppm; 33.1 ppm; 31.2 ppm; 25.7 ppm; 25.3 ppm; 25.1 ppm; 24.1 ppm 1.20

a₁ ¹³C-NMR: 166.5 ppm; 82.8 ppm; 33.4 ppm; 25.2 ppm; 23.4 ppm: 1.21

a₂ ¹³C-NMR: 167.2 ppm; 88.6 ppm; 62.5 ppm; 33.2 ppm; 30.8 ppm; 21.0 ppm 1.22

a₁ ¹³C-NMR: 166.5 ppm; 85.9 ppm; 33.2 ppm; 26.8 ppm; 22.5 ppm 1.23

1.24

1.25

1.26

1.27

a₂ ¹³C-NMR: 167.5 ppm; 136.0 ppm; 129.6 ppm; 129.2 ppm; 128.9 ppm; 127.5 ppm 1.28

1.29

1.30

1.31 —CH₂CH₂SC₂H₅ 1.32 —CH(CH₃)C₆F₅ 1.33

1.34 —CH₂C≡CH a₁ ¹³C-NMR: 167.7 ppm; 79.0 ppm; 75.3 ppm; 55.5 ppm 1.35

1.36

1.37

1.38

1.39

1.40 —CH₂CH₂COOC₂H₅ 1.41

1.42

1.43

1.44 —CH₂CH═CH₂ 1.45

1.46

1.47

1.48

1.49

1.50

1.51

a₂ ¹³C-NMR: 167.0 ppm; 166.8 ppm; 84.3 ppm; 45.7 ppm; 26.4 ppm; 9.5 ppm 1.52 —CH₂CH₂OCH₃ 1.53 —CH₂CH₂Br 1.54

a₂ ¹H-NMR: 3.9-4.1 ppm (3 H); 1.6-2.0 ppm (2 H); 1.05 ppm (3 H) 1.55

1.56

1.57

1.58

1.59

1.60

1.61

1.62

1.63

1.64

1.65

1.66

1.67

1.68

1.69

1.70

1.71

1.72

1.73

1.74

1.75

1.76

1.77

a₂ Melting point 67-68° C. 1.78

1.79

1.80

1.81

1.82

1.83 —(CH₂)₇CH₃ 1.84

1.85

a₂ ¹H-NMR: 8.2 ppm (2 H); 7.6 ppm (1 H); 7.5 ppm (2 H); 4.85 ppm (1 H); 4.6 ppm (1 H); 4.4 ppm (1 H); 3.7 ppm (2 H) 1.86 —CH(CH₂Cl)₂ 1.87

1.88 —CH₂-adamantyl 1.89

1.90

1.91 —CH₂CH₂CN 1.92

1.93

1.94

1.95

1.96

a₂ Oil 1.97

1.98

1.99

1.100 —CH₂CH₂CH(C₂H₅)₂ 1.101 —CH(C₂H₅)₂ 1.102 —CH₂CH(CH₃)Cl 1.103

1.104

1.105

1.106

1.107

1.108

1.109

1.110

1.111

1.112

1.113

1.114

1.115 —CH₂C₆F₅ 1.116

1.117 —CH₂CH₂Si(CH₃)₃ 1.118

1.119

1.120

1.121

1.122

1.123

1.124

1.125 —CH₂CH₂OCOCH₃ 1.126

1.127

1.128

1.129

1.130

1.131

1.132

1.133

1.134

1.135

1.136

1.137

Example H4 Preparation of 1-chloroethoxy-2-chloro-3-(2′-carboethoxyphenoxy)thiatriazine

3.32 g (0.02 mol) of ethyl salicylate are stirred with 0.96 9 of 55% sodium hydride (0.022 mol) in 50 ml of tetrahydrofuran under nitrogen. With evolution of hydrogen, a clear solution forms, which is added dropwise to a solution of 4.97 g (0.02 mol) of 1-chloroethoxy-3,5-dichlorothiatriazine at −30° C. The mixture is warmed to room temperature and extracted with water and ethyl acetate at pH 6, with addition of a little acetic acid. After the solvent has been evaporated, 7.2 g of crude product are obtained, which is chromatographed on silica gel with a mixture of ethyl acetate and hexane 3/7. The desired product is obtained as an oil in a yield of 6.6 g (95% of theory).

The compounds listed in the following Table 2 can be prepared analogously to Example H4.

TABLE 2 Compounds of the formula VI (VI)

Comp. No. R₇ R₃ Physical Data 2.1 —C₅H₁₁(n)

2.2 —CH₂CHCl₂ —SC₆Cl₅ Melting point 128-129° C. 2.3

2.4 —CH₂CH₂Cl

¹H-NMR: 7.2-8.1 ppm (4 H); 3.6-4.4 ppm (6 H); 1.4 ppm (3 H) 2.5

2.6

2.7

—OC₆F₅ 2.8 —CH₂CH₂Cl

¹³C-NMR: 169.8 ppm; 166.5 ppm; 150.9 ppm; 129.7 ppm; 126.7 ppm; 121.5 ppm; 66.1 ppm; 41.4 ppm 2.9 —CH₂C≡CH

2.10

¹³C-NMR: 169.2 ppm; 164.8 ppm; 139-148 ppm; 103.7 ppm; 84.5 ppm 2.11

—OC₆F₅ 2.12

2.13

¹³C-NMR: 168.9 ppm; 165.2 ppm; 155.7 ppm; 145.7 ppm; 125.4 ppm; 122.7 ppm; 81.4 ppm; 33.4 ppm; 24.8 ppm; 23.5 ppm 2.14 —CH₂CH₂OCH₃

2.15

2.16 —CH₂CH═CH₂

2.17

2.18

¹³C-NMR: 169.7 ppm; 167.0 ppm; 118.6-148.6 ppm; 70.0 ppm; 59.5 ppm 2.19

2.20

2.21

2.22

2.23

—SC₆F₅ 2.24

¹³C-NMR: 169.7 ppm; 166.4 ppm; 152.1 ppm; 151.6 ppm; 130.0 ppm; 110.6 ppm; 108.8 ppm; 105.0 ppm 2.25

2.26

2.27

2.28

2.29 —CH₂COOC₂H₅

2.30

¹H-NMR: 6.9-7.3 ppm (4 H); 4.4 ppm (1 H); 4.0 ppm (1 H); 3.8 ppm (3 H); 1.2-2.2 ppm (12 H) 2.31 —CH(CH₃)₂

2.32 —CH₂CH₂Cl —SC₆F₅ Melting point 72-73° C. 2.33 —CH₂CH₂Cl

2.34 —CH₂CH₂Cl

2.35 —CH₂CH₂Cl

2.36 —CH₂CH₂Cl

2.37 —CH₂CH₂Cl

2.38 —CH₂CH₂Cl

2.39 —CH₂CH₂Cl

2.40 —CH₂CH₂Cl

2.41

—OC₆F₅ 2.42

2.43

2.44

—OC₆F₅ 2.45

—OC₆F₅ 2.46

—SC₆F₅ 2.47 —CH₂CH₂Cl

2.48 —CH₂CH₂Cl

2.49 —CH₂CH₂Cl

¹H-NMR: 7.5-7.8 ppm (3 H); 5.55 ppm (1 H); 4.2 ppm (1 H); 3.9 ppm (1 H); 3.15 ppm (2 H); 1.6 ppm (3 H) 2.50 —CH₃

2.51 —CH(CH₃)₂

2.52 —CH₂CH₂F

2.53

2.54 —CH₂CH₂Cl

2.55 —CH₂CH₂Cl

2.56 —CH₂CH₂Cl

2.57 —CH₂CH₂Cl

2.58

2.59 —CH₂CH₂Br

2.60 —CH₂CH₂Cl

2.61 —CH₂CH₂Cl

2.62

2.63 —CH₂CH₂Cl

2.64 —CH₂CH₂Cl

2.65

2.66

2.67 —CH₂CH₂Br C₆F₅S— 2.68 —CH₂CH₂Cl

2.69 —CH₂CH₂Cl

2.70 —CH₂CH₂Cl

2.71 —CH₂CH₂Cl

2.72 —CH₂CH₂Cl

2.73 —CH₂CH₂F

2.74 —CH₂CH₂Cl

2.75 —CH₂CH₂OCH₃ C₆F₅O— 2.76 —CH₂CH═CH₂

2.77

C₆F₅O—

Example H5 Preparation of 1-(b-chloroethoxy)-3,5-diphenoxythiatriazine (process b₃)

2.07 g (0.022 mol) of phenol are dissolved in 30 ml of tetrahydrofuran under nitrogen at a temperature of 40° C. to 45° C., and 0.90 g (0.0225 mol) of 60% sodium hydride is added. When no further hydrogen is evolved, the mixture is cooled to −40° C., 2.5 g (0.01 mol) of 1-(b-chloroethoxy)-3,5-dichlorothiatriazine are added in portions and the exothermic reaction is allowed to proceed at −30° C. to −40° C. The temperature is then allowed to rise to 0° C. and the reaction mixture is extracted with water and ethyl acetate. After removal of the solvent, 4.5 g of crude product are obtained, which, after purification by chromatography (silica gel; ethyl acetate/hexane 1/1) and recrystallization from 10 ml of ethyl acetate and 15 ml of hexane, gives 3.35 g (92% of theory) of the desired pure product of melting point 89-90° C.

Analysis: C₁₆H₁₄ClN₃O₃S;

calculated found [%] [%] N 11.55 11.69 Cl  9.74  9.73

Example H6 Preparation of 1-cyclohexyloxy-3-(p-nitrophenoxy)-5-(a-naphthoxy)thiatriazine (process c₃)

0.65 g (0.0045 mol) of a-naphthol is dissolved in 40 ml of tetrahydrofuran, and 0.196 g (0.0045 mol) of 55% sodium hydride is added, under nitrogen. When the exothermic reaction has ended, the mixture is cooled to room temperature (23° C.) and a solution of 1.60 g (0.0043 mol) of 1-cyclohexyloxy-3-chloro-5-(p-nitrophenoxy)thiatriazine in a little tetrahydrofuran is added dropwise. During this operation, the temperature rises from 23° C. to 31° C. The mixture is extracted with water and ethyl acetate, the extract is concentrated and the residue is chromatographed (silica gel; ethyl acetate/hexane 1/9). This gives 1.05 g of the desired pure product, which is recrystallized from 5 ml of ethyl acetate and 5 ml of hexane. The yield of crystalline product of melting point 115-116° C. is 0.87 g. The ¹³C-NMR spectrum in CDCl₃ shows, in addition to the lines for the a-naphthyl radical (118-156 ppm), 4 lines for the cyclohexyl radical (79.3 ppm; 33.4 ppm; 24.9 ppm and 23.6 ppm) and 2 lines for the two C atoms of the thiatriazine ring (169.3 ppm and 168.2 ppm).

Example H7 Preparation of 1-(n-butoxy)-3,5-di(2′,5′-dichlorophenoxy)thiatriazine (process p)

0.75g (0.0015 mol) of 1-(b-chloroethoxy)-3,5-di(2′,5′-dichlorophenoxy)thiatriazine and 2.22 g (0.03 mol) of n-butanol are dissolved in 15 ml of tetrahydrofuran, the solution is cooled to −40° C. and 3.1 ml of a 0.098 molar solution of potassium tert-butylate in tetrahydrofuran (0.00030 mol) are added. After 45 minutes, the reaction has ended. The reaction mixture is extracted with water and ethyl acetate, the extract is concentrated and the residue is chromatographed (silica gel; ethyl acetate/hexane 8/92). The yield is 0.64 g (92% of theory) of a resin, the 300 MHz ¹H-NMR spectrum of which confirms the structure of the desired compound.

Example H8 Preparation of 1-(2,2-dimethylpropoxy)-3,5-di(pentafluorophenoxy)thiatriazine (process p)

0.74 g (0.001494 mol) of 1-methoxy-3,5-di(pentafluorophenoxy)thiatriazine is dissolved with 5.27 g (0.0598 mol) of 2,2-dimethyl-1-propanol in 15 ml of tetrahydrofuran, and 0.30 ml of a 0.0982 molar solution (2.94×10⁻⁵ mol) of potassium tert-butylate in tetrahydrofuran is added at −60° C. After 30 minutes, the reaction has ended. The mixture is extracted with water and ethyl acetate, the extract is concentrated on a rotary evaporator and the residue is treated under a high vacuum at 50° C. The yield is 0.75 g (91% of theory) of a resin, the 300 MHz ¹H— and ¹³C-NMR spectra of which are in agreement with the structure of the desired compound.

The compounds listed in the following Table 3 can be prepared analogously to Examples H5 to H8.

TABLE 3 Compounds of the formula V (V)

Comp. No. Process R₇ R₃ 3.1 b₃ —CH₂CH₂Cl

3.2 —CH₂CH₂Cl

3.3 b₃ —CH₂CH₂Cl C₆F₅O— 3.4 —CH₂CH₂Cl

3.5 b₃

3.6 b₃

C₆F₅O— 3.7 p —(CH₂)₃CH₃

3.8 —CH₂CH₂Cl

3.9 —CH₂CH₂Cl

3.10 p —CH₂CH₂C₆H₅

3.11 —CH₂CH₂Cl

3.12 —CH₂CH₂Cl

3.13 b₃ —CH₂CH₂Cl

3.14

3.15 —CH₂CH₂Cl

3.16 —CH₂CH₂Cl

3.17 —CH₂CH₂Cl

3.18

C₆F₅O— 3.19 b₃ —CH₂CH₂Cl

3.20 —CH₂CH₂F C₆F₅O— 3.21 —CH₂CH₂Cl

3.22 —CH₂CH₂Cl

3.23 b₃ —CH₂CH₂Cl C₆F₅S— 3.24 c₃

3.25 —CH₂CH₂Cl

3.26

3.27

3.28 b₃ —CH₂CH₂Cl

3.29 —CH₂CH₂Cl

3.30 —CH₂CH₂Cl

3.31 c₃

3.32

3.33 —CH₂C≡CH

3.34 —CH₂CH₂Cl

3.35 —CH₂CH₂Cl

3.36 p

3.37 —CH₂CH₂Cl

3.38 —CH₂CH₂Cl

3.39

3.40 p

C₆F₅S— 3.41 —CH₂CH₂Cl

3.42 —CH₂CH₂Cl

3.43 —CH₂CH₂Cl

3.44 —CH₂CH₂Cl

3.45 b₃ —CH₂CH₂Cl

3.46

C₆F₅O— 3.47 —CH₂CH₂Cl

3.48 p

3.49 —CH₂CH₂Cl

3.50 b₃ —CH₂CH₂Cl

3.51 —CH₂CH₂Cl

3.52 —CH₂CH₂Cl

3.53

3.54 —CH₂CH₂Cl C₆F₅O— 3.55 —CH₂CH₂Cl

3.56

3.57 c₃

C₆F₅O— 3.58 —CH₂CH₂Cl

3.59

3.60 —CH₂CH₂Cl

3.61 p —CH₃

3.62

3.63 —CH₂CH₂Cl

3.64 —CH₂CH₂Cl

3.65 —CH₂CH₂Cl

3.66 —CH₂CH₂Cl

3.67 b₃

C₆F₅O— 3.68 b₃ —CH₂CH₂Cl

3.69 —CH₂CH₂Cl

3.70 —CH₂CH₂Cl

3.71

3.72 p —CH₃ C₆F₅O— 3.73 —CH₂CH₂Cl

3.74 —CH₂CH₂Cl

3.75 —CH₂CH₂Cl

3.76

3.77 b₃ —CH₂CH₂Cl

3.78 —CH₂CH₂Cl

3.79 —CH₂CH₂Cl

3.80

3.81 —CH₂CH₂Cl

3.82 b₃ —CH₂CH₂Cl

3.83 —CH₂CH₂Cl

3.84 p —CH₂C(CH₃)₃ C₆F₅O— 3.85 —CH₂CH₂Cl

3.86

3.87 —CH₂CH₂Cl

3.88 —CH₂CH₂Cl

3.89 b₃

3.90 —CH₂CH₂Cl

3.91 —CH₂CH₂Cl

3.92 —CH₂CH₂Cl

3.93 b₃ —CH₂CH₂Cl

3.94 —CH₂CH₂Cl

3.95 —CH₂CH₂Cl

3.96 —CH₂CH₂Cl

3.97 b₃

3.98 —CH₂CH₂Cl

3.99

3.100 —CH₂CH₂Br C₆F₅O— 3.101 —CH₂CH₂Cl

3.102 —CH₂CH₂Cl

3.103 p —CH₃

3.104 —CH₂CH₂Cl

3.105 b₃ —CH₂CH₂Cl

3.106 —CH₂CH₂Cl

3.107 —CH₂CH₂Cl

3.108 —CH₂CH₂Cl

3.109 c₃

3.110 —CH₂CH₂Cl

3.111 —CH₂CH₂Cl

3.112 b₃ —CH₂CH₂Cl

3.113 —CH₂CH₂Cl

3.114

3.115 —CH₂CH₂Cl

3.116 —CH₂CH₂Cl

3.117 —CH₂CH₂Cl

3.118 —CH₂CH₂Cl

3.119 b₃

3.120

3.121 —CH₂CH₂Cl

3.122 —CH₂CH₂Cl

3.123 —CH₂CH₂Cl

3.124 p —CH(CH₃)(CH₂)₅CH₃

3.125 —CH₂CH₂Cl

3.126 —CH₂CH₂Cl

3.127 —CH₂CH₂Cl

3.128 —CH₂CH₂Cl

3.129 b₃ —CH₂CH₂Cl

3.130 b₃

—OC₆F₅ 3.131 b₃

—OC₆F₅ 3.132 —CH₂CH₂Cl

3.133 —CH₂CH₂Cl

3.134 —CH₂CH₂Cl

3.135 —CH₂CH₂Cl

3.136 b₃ —CH₂CH₂Cl

3.137 —CH₂CH₂Cl

3.138 —CH₂CH₂Cl

3.139 —CH₂CH₂Cl

3.140 b₃ —CH₂CH₂Cl

3.141 —CH₂CH₂Cl

3.142 b₃ —CH₂CH₂Cl

3.143

3.144 —CH₂CH₂Cl

3.145 —CH₂CH₂Cl

3.146 —CH₂CH₂Cl C₆F₅O— 3.147 b₃

3.148 —CH₂CH₂Cl

3.149 —CH₂CH₂Cl

3.150 —CH₂CH₂Cl

3.151 —CH₂CH₂Cl C₆F₅O— 3.152 —CH₂CH₂Cl

3.153

3.154 —CH₂CH₂Cl

3.155 b₃ —CH₂CH₂Cl

3.156 —CH₂CH₂Cl

3.157

3.158 —CH₂CH₂Cl

3.159

3.160 b₃ —CH₂CH₂Cl

3.161 —CH₂CH₂Cl C₆F₅O— 3.162 —CH₂CH₂Cl

3.163

3.164 —CH₂CH₂Cl

3.165 —CH₂CH₂Cl

3.166 —CH₂CH₂Cl

3.167 —CH₂CH₂Cl

3.168 c₃

3.169 p —CH₂CH₂CH₃

3.170 —CH₂CH₂Cl

3.171 —CH₂CH₂Cl C₆F₅O— 3.172 —CH₂CH₂Cl

3.173 —CH₂CH₂Cl

3.174

3.175 —CH₂CH₂Cl

3.176 CH₂CH₂Cl

3.177 —CH₂CH₂Cl

3.178 —CH₂CH₂Cl

3.179 b₃ —CH₂CH₂Cl

3.180 —CH₂CH₂Cl C₆F₅O— 3.181 —CH₂CH₂Cl

3.182

3.183 —CH₂CH₂Cl

3.184

3.185 —CH₂CH₂Cl

3.186 p

3.187 —CH₂CH₂Cl

3.188 —CH₂CH₂Cl

3.189 p

C₆F₅O— 3.190 —CH₂CH₂Cl

3.191

3.192 —CH₂CH₂Cl

3.193 —CH₂CH₂Cl

3.194

3.195 —CH₂CH₂Cl

3.196 b₃ —CH₂CH₂Cl

3.197 —CH₂CH₂Cl

3.198

3.199 —CH₂CH₂Cl

3.200

3.201 —CH₂CH₂Cl

3.202 p —C₂H₅

3.203 —CH₂CH₂Cl

3.204 —CH₂CH₂Cl C₆F₅O— 3.205 —CH₂CH₂Cl

3.206 —CH₂CH₂Cl

3.207 p —(CH₂)₄CH₃

3.208 —CH₂CH₂Cl

3.209 —CH₂CH₂Cl

3.210

3.211 —CH₂CH₂Cl

3.212 —CH₂CH₂Cl

3.213 —CH₂CH₂Cl

3.214

3.215 —CH₂CH₂Cl

3.216 —CH₂CH₂Cl

3.217

3.218 —CH₂CH₂Cl

3.219 p

3.220 —CH₂CH₂Cl

3.221 —CH₂CH₂Cl

3.222 —CH₂CH₂Cl

3.223

C₆F₅O— 3.224

C₆F₅O— 3.225

3.226

3.227

C₆F₅O— 3.228

C₆F₅O— 3.229

3.230

C₆F₅O— 3.231

3.232 p

—OC₆F₅ 3.233 p —CH₂CH₂Si(CH₃)₃ —OC₆F₅ 3.234 p

—OC₆F₅ 3.235 p —(CH₂)₃Si(CH₃)₃ —OC₆F₅ 3.236 p

—OC₆F₅ 3.237 p

—OC₆F₅ 3.238 p —CH₂C₆F₅ —OC₆F₅ 3.239 p

—OC₆F₅ 3.240 p

—OC₆F₅ 3.241 p —CH₂Si(CH₃)₃ —OC₆F₅ 3.242 p

—OC₆F₅ 3.243 p

—OC₆F₅ 3.244 p

—OC₆F₅ 3.245 p —CH(CH₃)C₆F₅ —OC₆F₅ 3.246 p

—OC₆F₅ 3.247 p

—OC₆F₅ 3.248 p —CH(CH₃)Si(CH₃)₃ —OC₆F₅ 3.249 p

—OC₆F₅ 3.250 —CH(CH₃)COOCH₃ —OC₆F₅ 3.251 b₃ —CH₂CH₂Cl

3.252 p —C₂H₅ —SC₆F₅ 3.253 p —CH₃ —SC₆F₅ 3.254 p —CH(CH₃)₂ —SC₆F₅ 3.255 p —CH₂CH₂Si(CH₃)₃ —OCH₂CH₂Cl 3.256 p —CH₂CH₂CH₂Si(CH₃)₃ —OCH₂CH₂Cl 3.257 p Adamantyl —OCH₂CH₂Cl 3.258 p —CH₂Si(CH₃)₃ —OCH₂CH₂Cl 3.259 p

—OC₆F₅ 3.260 p —CH(CH₃)Si(CH₃)₃ —OC₆F₅ 3.261 p

3.262 p

3.263 p

3.264 p —CH₂Si(CH₃)₃

3.265 p

3.266

3.267 p

3.268 p

3.269 p

3.270 p

—OC₆F₅ 3.271

—OC₆F₅ 3.272

—OC₆F₅ 3.273 p

—OC₆F₅ 3.274 p

—OC₆F₅ 3.275 p

—OC₆F₅ 3.276 p

—OC₆F₅ 3.277 p

—OC₆F₅ 3.278 p

—OC₆F₅ 3.279 p

—OC₆F₅ 3.280

—OC₆F₅ 3.281 p

—OC₆F₅ 3.282

—OC₆F₅ 3.283

—OC₆F₅ 3.284 p

—OC₆F₅ 3.285 p

—OC₆F₅ 3.286 p

—OC₆F₅ 3.287 p

—OC₆F₅ 3.288 p

—OC₆F₅ 3.289

—OC₆F₅ 3.290

—OC₆F₅ 3.291

—OC₆F₅ 3.292 p

—OC₆F₅ 3.293

—OC₆F₅ 3.294

—OC₆F₅ 3.295 p

—OC₆F₅ 3.296 p

—OC₆F₅ 3.297

—OC₆F₅ 3.298

—OC₆F₅ 3.299 p

—OC₆F₅ 3.300

—OC₆F₅ 3.301

—OC₆F₅ 3.302

—OC₆F₅ 3.303

—OC₆F₅ 3.304

—OC₆F₅ 3.305

—OC₆F₅ 3.306

—OC₆F₅ 3.307

—OC₆F₅ 3.308

—OC₆F₅ Comp. No. R₁₂—X₁ 3.1

3.2

3.3 C₆F₅O— 3.4 C₆F₅S— 3.5

3.6 C₆F₅O— 3.7

3.8

3.9

3.10

3.11

3.12 C₆F₅S— 3.13

3.14

3.15 C₆F₅S— 3.16

3.17 C₆Cl₅O— 3.18 C₆F₅O— 3.19

3.20 C₆F₅O— 3.21

3.22

3.23 C₆F₅S— 3.24

3.25

3.26

3.27

3.28

3.29

3.30

3.31

3.32

3.33

3.34

3.35

3.36

3.37

3.38

3.39

3.40 C₆F₅S— 3.41

3.42

3.43

3.44

3.45

3.46 C₆F₅O— 3.47

3.48

3.49

3.50

3.51

3.52

3.53

3.54

3.55

3.56

3.57

3.58

3.59

3.60

3.61

3.62

3.63

3.64

3.65

3.66

3.67 C₆F₅O— 3.68

3.69

3.70

3.71

3.72 C₆F₅O— 3.73

3.74

3.75

3.76

3.77

3.78

3.79

3.80

3.81

3.82

3.83

3.84 C₆F₅O— 3.85

3.86

3.87

3.88

3.89

3.90

3.91

3.92

3.93

3.94

3.95

3.96

3.97

3.98

3.99

3.100 C₆F₅O— 3.101

3.102

3.103

3.104

3.105

3.106

3.107

3.108

3.109 —SC₆F₅ 3.110

3.111

3.112

3.113

3.114

3.115

3.116

3.117

3.118

3.119

3.120

3.121

3.122

3.123

3.124

3.125

3.126

3.127

3.128

3.129

3.130 —OC₆F₅ 3.131 —OC₆F₅ 3.132

3.133

3.134

3.135

3.136

3.137

3.138

3.139

3.140

3.141

3.142

3.143

3.144

3.145

3.146

3.147

3.148

3.149 C₆F₅S— 3.150 C₆F₅O— 3.151

3.152

3.153

3.154

3.155

3.156

3.157

3.158

3.159

3.160

3.161

3.162

3.163

3.164 C₆F₅O— 3.165

3.166

3.167

3.168 —C₆F₅S— 3.169

3.170 C₆F₅O— 3.171 C₆F₅S— 3.172

3.173

3.174

3.175

3.176

3.177

3.178

3.179

3.180

3.181

3.182

3.183

3.184

3.185

3.186

3.187

3.188

3.189 C₆F₅O— 3.190

3.191

3.192

3.193

3.194

3.195

3.196

3.197

3.198

3.199

3.200

3.201

3.202

3.203

3.204

3.205

3.206

3.207

3.208

3.209

3.210

3.211

3.212

3.213 C₆F₅O— 3.214

3.215

3.216

3.217

3.218

3.219

3.220

3.221

3.222

3.223 C₆F₅O— 3.224 C₆F₅O— 3.225

3.226

3.227 C₆F₅O— 3.228 C₆F₅O— 3.229

3.230 C₆F₅O— 3.231

3.232 —OC₆F₅ 3.233 —OC₆F₅ 3.234 —OC₆F₅ 3.235 —OC₆F₅ 3.236 —OC₆F₅ 3.237 —OC₆F₅ 3.238 —OC₆F₅ 3.239 —OC₆F₅ 3.240 —OC₆F₅ 3.241 —OC₆F₅ 3.242 —OC₆F₅ 3.243 —OC₆F₅ 3.244 —OC₆F₅ 3.245 —OC₆F₅ 3.246 —OC₆F₅ 3.247 —OC₆F₅ 3.248 —OC₆F₅ 3.249 —OC₆F₅ 3.250 —OC₆F₅ 3.251

3.252 —SC₆F₅ 3.253 —SC₆F₅ 3.254 —SC₆F₅ 3.255 —OC₆F₅ 3.256 —OC₆F₅ 3.257 —OC₆F₅ 3.258 —OC₆F₅ 3.259 —OC₆F₅ 3.260 —OC₆F₅ 3.261

3.262

3.263

3.264

3.265

3.266

3.267

3.268

3.269

3.270 —OC₆F₅ 3.271 —OC₆F₅ 3.272 —OC₆F₅ 3.273 —OC₆F₅ 3.274 —OC₆F₅ 3.275 —OC₆F₅ 3.276 —OC₆F₅ 3.277 —OC₆F₅ 3.278 —OC₆F₅ 3.279 —OC₆F₅ 3.280 —OC₆F₅ 3.281 —OC₆F₅ 3.282 —OC₆F₅ 3.283 —OC₆F₅ 3.284 —OC₆F₅ 3.285 —OC₆F₅ 3.286 —OC₆F₅ 3.287 —OC₆F₅ 3.288 —OC₆F₅ 3.289 —OC₆F₅ 3.290 —OC₆F₅ 3.291 —OC₆F₅ 3.292 —OC₆F₅ 3.293 —OC₆F₅ 3.294 —OC₆F₅ 3.295 —OC₆F₅ 3.296 —OC₆F₅ 3.297 —OC₆F₅ 3.298 —OC₆F₅ 3.299 —OC₆F₅ 3.300 —OC₆F₅ 3.301 —OC₆F₅ 3.302 —OC₆F₅ 3.303 —OC₆F₅ 3.304 —OC₆F₅ 3.305 —OC₆F₅ 3.306 —OC₆F₅ 3.307 —OC₆F₅ 3.308 —OC₆F₅

Physical data of compounds in Table 3:

Comp. No. Physical Data 3.1 Melting point 89-90° C. 3.3 Melting point 82-83° C. 3.5 ¹H-NMR: 6.9-7.3 ppm (8H); 4.3 ppm (1H); 3.95 ppm (1H); 3.8 ppm (6H); 1.2-2.2 ppm (12H) 3.6 Melting point 104-105° C. 3.7 ¹H-NMR: 7.3 ppm (2H); 7.1 ppm (4H); 3.8 ppm (2H); 1.6 ppm (2H); 1.4 ppm (2H); 0.9 ppm (3H) 3.10 ¹H-NMR: 6.8-7.4 ppm (6H); 3.9 ppm (2H); 3.0 ppm (2H) 3.13 Melting point 184-186° C. 3.19 ¹H-NMR: 7.1-8.0 ppm (8H); 4.1 ppm (2H); 3.6 ppm (2H); 3.35 ppm (3H) 3.23 Melting point 89-90° C. 3.24 ¹H-NMR: 7.6 ppm (2H); 7.4 ppm (1H); 6.9 ppm (1H); 5.5 ppm (1H); 4.4 ppm (1H); 1.4-1.9 ppm (14H) 3.28 ¹H-NMR: 10.05 ppm (2H); 7.1-7.9 ppm (8H); 4.1 ppm (2H); 3.65 ppm (2H) 3.31 Melting point 115-116° C. 3.36 ¹H-NMR: 7.6-7.7 ppm (2H); 7.1-7.3 ppm (4H); 5.3-5.5 ppm (1H); 4.3-4.5 ppm (1H) 3.40 ¹³C-NMR: 173.8 ppm; 135-150 ppm; 79.0 ppm 22.0-47.4 ppm (7 signals) 3.45 Melting point 83-84° C. 3.48 ¹H-NMR: 6.5-7.4 ppm (11H); 5.7 ppm (1H); 1.6 ppm (3H) 3.50 ¹H-NMR: 7.05 ppm (2H); 6.85 ppm (2H); 4.7 ppm (2H); 4.2 ppm (4H); 4.0 ppm (2H) 3.6 ppm (2H); 1.6 ppm (6H); 1.3 ppm (6H) 3.57 ¹H-NMR: 7.1-7.9 ppm (12H); 4.95 ppm (1H); 4.1 ppm (2H) 3.61 Melting point 100-102° C. 3.67 ¹³C-NMR: 167.9 ppm; 136-143 ppm; 86.7 ppm; 62.5 ppm; 33.4 ppm; 30.6 ppm; 21.0 ppm 3.68 Melting point 141-142° C. 3.72 Melting point 86-87° C. 3.77 ¹H-NMR: 8.85 ppm (2H); 7.4 ppm (2H); 7.15 ppm (2H); 4.05 ppm (2H); 3.6 ppm (2H); 2.6 ppm (6H) 3.82 ¹H-NMR: 7.9 ppm (2H); 7.6 ppm (2H); 7.4 ppm (4H); 4.0 ppm (2H); 3.9 ppm (6H); 3.6 ppm (2H) 3.84 ¹³C-NMR: 168.2 ppm; 136-143 ppm; 73.8 ppm; 31.6 ppm; 25.9 ppm 3.89 Melting point 126-127° C. 3.93 Melting point 173-174° C. 3.97 Melting point 108-109° C. 3.103 Melting point 100-102° C. 3.105 Melting point 169-170° C. 3.109 ¹³C-NMR: 177.9 ppm; 162.9 ppm; 103.2 ppm; 83.5 ppm 3.112 ¹H-NMR: 8.6 ppm (2H); 7.7 ppm (4H); 7.3 ppm (2H); 4.0 ppm (2H); 3.6 ppm (2H) 3.119 Melting point 80-81° C. 3.124 ¹H-NMR: 7.1-7.3 ppm (6H); 4.35 ppm (1H); 1.6 ppm (2H); 1.3 ppm (11H); 0.9 ppm (3H) 3.129 ¹H-NMR: 6.4 ppm (2H); 6.3 ppm (4H); 4.0 ppm (2H); 3.8 ppm (12H); 3.6 ppm (2H) 3.130 ¹³C-NMR: 167.4 ppm; 147.7 ppm; 109.7 ppm; 88.2 ppm; 62.2 ppm; 36.5 ppm; 34.0 ppm; 32.0 ppm; 26.3 ppm; 25.4 ppm; 20.6 ppm 3.131 ¹³C-NMR: 167.4 ppm; 147.8 ppm; 109.5 ppm; 83.1 ppm; 68.1 ppm; 37.1 ppm; 35.7 ppm; 33.0 ppm; 29.5 ppm; 26.2 ppm; 20.5 ppm 3.136 Melting point 96-97° C. 3.140 Melting point 86-87° C. 3.142 ¹H-NMR: 7.3 ppm (2H); 7.15 ppm (4H); 4.0 ppm (2H); 3.6 ppm (2H) 3.147 ¹H-NMR: 7.2 ppm (2H); 6.6 ppm (2H); 6.4 ppm (2+2H); 4.4 ppm (1H); 3.7 ppm (2H); 3.5 ppm (2H); 2.9 ppm (12H) 3.155 Melting point 101-102° C. 3.160 ¹H-NMR: 7.1 ppm (2H); 6.9 ppm (4H); 4.0 ppm (2H); 3.6 ppm (2H) 3.168 ¹³C-NMR: 177.9 ppm; 162.9 ppm; 103.2 ppm; 83.5 ppm 3.169 Melting point 197-198° C. 3.179 Melting point 100-101° C. 3.186 ¹H-NMR: 6.8-7.4 ppm (6H); 4.7 ppm (2H) 3.189 ¹³C-NMR: 167.8 ppm; 136.2-143.1 ppm; 83.2 ppm; 34.0 ppm; 23.2 ppm 3.196 Melting point 106-108° C. 3.202 Melting point 89-90° C. 3.207 ¹H-NMR: 6.9-7.2 ppm (6H); 3.7 ppm (2H) 1.7 ppm (2H); 1.3 ppm (4H); 0.9 ppm (3H) 3.219 ¹H-NMR: 6.8-7.1 ppm (6H); 4.15 ppm (1H) 1.2-1.9 ppm (10H) 3.224 Melting point 85-86° C. 3.232 ¹³C-NMR: 168.2 ppm; 142.4 ppm; 120.3 ppm; 63.3 ppm; 45.6 ppm; 40.6 ppm; 38.0 ppm; 36.3 ppm; 31.5 ppm; 31.3 ppm; 26.1 ppm; 21.0 ppm 3.233 ¹³C-NMR: 168.1 ppm; 136-143 ppm; 64.2 ppm; 18.2 ppm; −1.9 ppm 3.234 Melting point 126-127° C. 3.235 ¹³C-NMR: 168.1 ppm; 136-143 ppm; 68.0 ppm; 24.0 ppm; 12.3 ppm; −1.99 ppm 3.236 Melting point 99-100° C. 3.237 ¹³C-NMR: 171.4 ppm; 168.2 ppm; 137.6 ppm; 136.2-142.8 ppm; 62.0 ppm; 36.8 ppm; 8.6 ppm 3.239 Melting point 113-114° C. 3.240 Melting point 93-94° C. 3.241 ¹³C-NMR: 168.53 ppm; 54.59 ppm; −3.54 ppm; 3.243 ¹³C-NMR: 167.9 ppm; 167.6 ppm; 119.1 ppm; 84.1 ppm; 44.2 ppm; 33.6 ppm; 28.4 ppm; 24.9 ppm; 21.7 ppm; 15.8 ppm 3.244 ¹³C-NMR: 168.0 ppm; 167.7 ppm; 119.0 ppm; 85.8 ppm; 45.7 ppm; 32.6 ppm; 28.7 ppm; 28.5 ppm; 22.1 ppm; 21.7 ppm; 15.8 ppm 3.246 ¹³C-NMR: 167.7 ppm; 81.2 ppm; 33.6 ppm; 33.0 ppm; 31.2 ppm; 21.5 ppm 3.247 ¹³C-NMR: 167.7 ppm; 78.2 ppm; 31.3 ppm; 30.9 ppm; 28.6 ppm; 21.7 ppm 3.248 Melting point 48-49° C. 3.249 ¹H-NMR: 5.8 ppm (1H); 5.0 ppm (2H); 4.2 ppm (1H); 0 ppm (9H) 3.251 Melting point 185-186° C. 3.252 ¹³C-NMR: 174.5 ppm; 62.5 ppm; 15.0 ppm; 3.253 Melting point 90-92° C. 3.254 ¹³C-NMR: 173.8 ppm; 75.7 ppm; 23.6 ppm; 3.255 ¹H-NMR: 4.55 ppm (2H); 3.2 ppm (4H); 1.0 ppm (2H); 0 ppm (9H) 3.256 ¹H-NMR: 4.6 ppm (2H); 3.75 ppm (2H); 3.6 ppm (2H); 1.6 ppm (2H); 0.5 ppm (2H); 0 ppm (9H) 3.257 ¹H-NMR: 4.6 ppm (2H); 3.8 ppm (2H); 3.2 ppm (2H); 2.0 ppm (3H); 1.4-1.8 ppm (6H) 3.258 ¹H-NMR: 4.5 ppm (2H); 3.7 ppm (2H); 3.0 ppm (2H); 0 ppm (9H) 3.259 ¹³C-NMR: 167.7 ppm; 78.2 ppm; 31.3 ppm; 30.9 ppm; 28.6 ppm; 21.7 ppm 3.260 Melting point 48-49° C. 3.261 Melting point 95-96° C. 3.262 Melting point 131-132° C. 3.263 ¹H-NMR: 7.0 ppm (2H); 4.55 ppm (1H); 0.8-2.0 ppm (16H) 3.264 Melting point 83-84° C. 3.265 Melting point 103-104° C. 3.267 ¹³C-NMR: 167.7 ppm; 138.9-147.6 ppm; 103.1-103.7 ppm; 51.0 ppm; 46.3 ppm; 34.7 ppm; 32.9 ppm; 27.5 ppm 3.268 Melting point 74-75° C. 3.269 Melting point 112-113° C. 3.270 ¹³C-NMR: 167.7 ppm; 136-143 ppm; 81.9 ppm; 35.0 ppm; 34.4 ppm; 33.9 ppm; 31.2 ppm; 28.9 ppm; 26.1 ppm; 21.1 ppm 3.273 ¹³C-NMR: 168.0 ppm; 167.8 ppm; 139.0 ppm; 130.7 ppm; 125-143.0 ppm; 79.6 ppm; 47.6 ppm; 47.5 ppm; 42.2 ppm; 35.1 ppm 3.274 ¹³C-NMR: 168.0 ppm; 187.8 ppm; 142.3 ppm; 131.6 ppm; 80.4 ppm; 49.0 ppm; 46.0 ppm; 40.7 ppm; 35.3 ppm 3.275 ¹³C-NMR: 167.8 ppm; 125-143 ppm; 75.9 ppm; 36.3 ppm (q); 30.8 ppm; 30.7 ppm; 29.6 ppm; 23.7 ppm; 18.4 ppm 3.276 ¹³C-NMR: 168.1 ppm; 138.3 ppm; 131.4 ppm; 125-143 ppm; 68.4 ppm; 49.4 ppm; 43.7 ppm; 42.3 ppm; 38.2 ppm; 29.1 ppm 3.277 ¹³C-NMR: 167.8 ppm; 125-143 ppm; 80.7 ppm; 42.0 ppm; 37.4 ppm; 37.3 ppm; 36.4 ppm; 29.0 ppm; 20.6 ppm 3.278 ¹³C-NMR: 167.8 ppm; 125-143 ppm; 83.1 ppm; 43.3 ppm; 40.3 ppm; 35.4 ppm; 34.9 ppm; 27.8 ppm; 24.1 ppm 3.279 ¹³C-NMR: 167.7 ppm; 127-143 ppm; 73.5 ppm; 45.5 ppm (q); 31.8 ppm; 23.9 ppm; 19.8 ppm; 19.5 ppm 3.281 ¹³C-NMR: 167.9 ppm; 167.4 ppm; 125-143 ppm; 81.8 ppm; 47.5 ppm; 44.8 ppm; 41.4 ppm; 38.4 ppm; 36.8 ppm; 33.9 ppm; 27.2 ppm; 23.7 ppm; 19.4 ppm 3.284 Melting point 123-124° C. 3.285 Melting point 117-118° C. 3.286 Melting point 109-110° C. 3.287 ¹³C-NMR: 167.9 ppm; 167.7 ppm; 136-143 ppm; 119.1 ppm; 83.0 ppm; 41.6 ppm; 33.4 ppm; 28.8 ppm; 21.8 ppm; 17.2 ppm 3.288 ¹³C-NMR: 167.9 ppm; 167.7 ppm; 136-143 ppm; 117.4 ppm; 84.3 ppm; 42.8 ppm; 32.5 ppm; 28.6 ppm; 21.9 ppm; 19.8 ppm 3.292 Melting point 82-83° C. 3.295 ¹³C-NMR: 167.5 ppm; 157.7 ppm; 136-143 ppm; 131.5 ppm; 128.6 ppm; 124.3 ppm; 120.5 ppm; 110.3 ppm; 78.6 ppm; 55.1 ppm; 38.8 ppm; 30.4 ppm; 21.4 ppm 3.296 ¹³C-NMR: 168.3 ppm; 126-143 ppm; 136.3 ppm; 135.2 ppm; 133.4 ppm; 129.6 ppm; 128.9 ppm; 127.5 ppm; 67.0 ppm; 39.9 ppm; 33.3 ppm; 20.0 ppm; 13.8 ppm 3.299 ¹³C-NMR: 168.4 ppm; 126-143 ppm; 65.9 ppm;

Example H9 Preparation of 1,3,5-trimethoxythiatriazine (process a₃)

2.04 g (0.02 mol) of trichlorothiatriazine are dissolved in 15 ml of tetrahydrofuran and a solution of 5.94 g (0.033 mol) of 30% methanolic sodium methylate solution in 20 ml of tetrahydrofuran is added dropwise at 30° C., while cooling. After 15 minutes, the reaction mixture is extracted with water and ethyl acetate, the extract is concentrated and the residue is chromatographed over silica gel with ethyl acetate/hexane 1/3 as the eluting agent. The yield of the desired product is 1.70 g (89% of theory).

Analysis: C₅H₉N₃O₃S;

calculated [%] found [%] N 21.98 21.98 S 16.77 16.25

Example H10 Preparation of 1,3-dimethoxy-5-(2′,5′-difluorophenoxy)thiatriazine (process d₃)

3.05 g (0.007 mol) of 1-(β-chloroethoxy)-3,5-di(2′,5′-difluorophenoxy)thiatriazine are dissolved in 20 ml of methanol. 10.4 ml of a 1.35 molar sodium methylate solution in methanol are slowly added dropwise at −60° C., the intermediate 1-methoxy-3,5-di(2′,5′-difluorophenoxy)thiatriazine crystallizing out. The mixture is warmed gradually to +5° C., the intermediate reacting further to give the desired end product. The reaction mixture is extracted with water and ethyl acetate, the extract is concentrated and the residue is chromatographed over silica gel. The yield of desired product is 1.38 g (68% of theory). After recrystallization from a mixture of cyclohexane/toluene 6/1, the product melts at 75-76° C.

Analysis: C₁₀H₉N₃O₃F₂S;

calculated found [%] [%] C 41.52 41.68 H  3.14  3.19 N 14.53 14.44

0.30 g of 1,3,5-trimethoxythiatriazine (Example H9) is isolated as a by-product.

Example H11 Preparation of 1-(β-chloroethoxy)-3,5-di(trichloroethoxy)thiatriazine (process d₃)

1.80 g (0.0036 mol) of 1-(β-chloroethoxy)-3,5-di(2′,4′-dichlorophenoxy)thiatriazine are dissolved in 20 ml of tetrahydrofuran and the solution is cooled to −50° C. A solution prepared from 1.12 g (0.0075 mol) of trichloroethanol and 0.33 g of 55% sodium hydride (0.0075 mol) is added dropwise to this solution. The reaction is exothermic. The reaction mixture is warmed to 0° C., extracted with water and ethyl acetate, and the product is chromatographed over silica gel. The yield is 1.62 g (95% of theory). The desired compound is a resin, the ¹H— and ¹³C-NMR spectra of which confirm the structure.

Example H12 Preparation of 1-(β-chloroethoxy)-3,5-di-tert-butylmercaptothiatriazine and 1-(β-chloroethoxy)-3-chloro-5-tert-butylmercaptothiatriazine (process b₁)

3.00 g (0.012 mol) of 1-(β-chloroethoxy)-3,5-dichlorothiatriazine are dissolved in 20 ml of tetrahydrofuran, and a solution of 3.25 g (0.036 mol, of tert-butylmercaptan and 3.64 g (0.036 mol) of trethylamine in 15 ml of tetrahydrofuran is added dropwise at −50° C. Thereafter, the mixture warmed to 0° C., extracted with water and ethyl acetate, and the substance mixture is separated over silica gel with ethyl acetate/hexane 3/1 as the eluting agent. 1.05 g of 1-(β-chloroethoxy)-3-chloro-5-tert-butylmercaptothiatriazine and 0.25 g of 1-(β-chloroethoxy)-3,5-di-tert-butylmercaptothiatriazine are obtained as resins. The ¹H-NMR spectra and the mass spectra confirm the structures.

The compounds listed in the following Table 4 can be prepared analogously to Examples H9 to H12.

TABLE 4 Compounds of the formula IV (IV)

Comp. Proc- No. ess R₇ R₃ R₂ 4.1 c₂ —CH₃

—OCH₃ 4.2 a₃ —CH₃ —OCH₃ —OCH₃ 4.3

—OCH₃

4.4 b₁ —CH₂CH₂Cl Cl —SCH(CH₃)₂ 4.5 d₃ —CH₃

—OCH₃ 4.6 —C₂H₅ —OC₂H₅

4.7 —CH₃

—OCH₃ 4.8 d₃ —CH₂CH₂Cl —OC₂H₅ —OC₂H₅ 4.9 d₃ —CH₃

—OCH₃ 4.10

—SCH₃

4.11 —CH₂CH═CH₂ —OCH₂CH═CH₂

4.12 d₃ —CH₃

—OCH₂C≡CH 4.13 —CH₂CH₂Cl —SCH₃

4.14 —CH₂CH₂Cl

—SCH₃ 4.15 a₃ —Ch₂CH₂CH₃ Cl —OCH₂CH₂CH₃ 4.16 d₃ —CH₃ C₆F₅O— —OCH₃ 4.17 —CH₃ —OCH₃

4.18 b₁ —CH₂CH₂Cl —SCH(CH₃)₂ —SCH(CH₃)₂ 4.19

4.20 d₃ —C₂H₅

—OC₂H₅ 4.21

—OCH₃

4.22 b₁ —CH₂CH₂Cl Cl —SC(CH₃)₃ 4.23 d₃ —CH₂CH₂Cl —OCH₂CF₃ —OCH₂CF₃ 4.24 —CH₃

—OCH₃ 4.25

—SC₂H₅

4.26 a₃ —CH₂CH₂CH₃ —OCH₂CH₂CH₃ —OCH₂CH₂CH₃ 4.27 —CH₃

—OCH₃ 4.28 —CH(CH₃)₂ —O—CH(CH₃)₂

4.29 d₃ —CH₂CH₂Cl —OCH₂CBr₃ —OCH₂CBr₃ 4.30 —CH₂CH₂Cl —SCH₃

4.31 —CH₃

4.32 —C₄H₉(n) —OC₄H₉(n)

4.33 d₃ —C₂H₅ —OCH₃ —OCH₃ 4.34 —C₂H₅

—OC₂H₅ 4.35 —CH₃ —OC₆F₅

4.36 —CH₂CH₂Cl —OC(CH₃)₃

4.37 —CH₃

—OCH₃ 4.38 d₃ —CH₂CH₂Cl —OCH₂CCl₃ —OCH₂CCl₃ 4.39

—SCH₃ —SCH₃ 4.40 —CH(CH₃)₂ —O—CH(CH₃)₂

4.41 d₃ —C₂H₅

—OC₂H₅ 4.42 —CH₃ —OCH₃

4.43 d₃ —CH₃

—OCH₃ 4.44 —CH₃ —OCH₃

4.45 d₃

C₆F₅O— —CH₂CH₂Cl 4.46

—SC₂H₅ —SC₂H₅ 4.47 —CH₃

—OCH₃ 4.48 —CH(CH₃)₂ —O—CH(CH₃)₂

4.49 b₁ —CH₂CH₂Cl —SC(CH₃)₃ —SC(CH₃)₃ 4.50 d₃ —C₂H₅ —OC₂H₅ —OC₂H₅ 4.51

—OCH₃ —OCH₃ 4.52 —CH₂CH₂Cl C₆F₅O— —SCH₃ 4.53 —CH₂CH₂Cl

—OCH₃ 4.54 —CH₂CH₂Cl

—SCH(CH₃)₂ 4.55 —CH(CH₃)₂

—OCH(CH₃)₂ 4.56

—SCH₃ —SCH₃ 4.57 —CH₃

—OCH₃ 4.58

—OC₂H₅

4.59 —CH₂CH₂Cl —SCH₃

4.60 —CH₂C≡CH C₆F₅O— —OCH₃ 4.61 —CH₂C≡CH

—OCH₃ 4.62

C₆F₅O— —SCH₃ 4.63 —C₂H₅

—OC₂H₅ 4.64 —CH₂CH₂Cl —SCH₃

4.65 —CH₃ —OCH₃

4.66 —CH₃

—OCH₃ 4.67

—S—CH(CH₃)₂ —S—CH(CH₃)₂ 4.68 —CH₃ —OCH₃

4.69

C₆F₅O— —OCH₃ 4.70 —CH₂CH₂Cl

—SCH₃ 4.71 —CH₂CH₂Cl

—OCH(CH₃)C₂H₅ 4.72

—SC(CH₃)₂ —SC(CH₃)₃ 4.73 —CH₃ —OCH₃

4.74 —CH₃

—OCH₃ 4.75 —C₂H₅ —OC₂H₅

4.76 —CH(CH₃)₂

—O—CH(CH₃)₂ 4.77 —CH₃ —SCH₃

4.78 —CH₃ —OCH₃

4.79 —C₃H₇(n)

—OC₃H₇(n) 4.80

—SCH₃ —SCH₃ 4.81 —CH₃

—OCH₃ 4.82 —CH₃ —OCH₃

4.83

—SC₂H₅ —SC₂H₅ 4.84 —CH₂CH₂Cl

—SCH₃ 4.85 —CH₂CH₂Cl

4.86 d₃ —CH₃ —OCH₃

4.87

—SC₄H₉(n) 4.88 —CH₃

—OCH₃ 4.89

4.90 —CH(CH₃)C₂H₅ —OCH(CH₃)C₂H₅

4.91

C₆F₅O— —OCH₃ 4.92 —CH₃

—OCH₃ 4.93 —CH₂CH═CH₂ —SCH₃ —SCH₃ 4.94 —CH₂CH═CH₂

—OCH₃ 4.95

C₆F₅O— —OCH₃ 4.96 —CH₂CH₂Cl —OCH₃

4.97 —CH₂CH₂Cl

—SCH₃ 4.98 —C₂H₅ —OC₂H₅

4.99 —CH₃

—OCH₃ 4.100 —CH₃

—SCH₃ 4.101

—SC₂H₅

4.102 —CH(CH₃)₂

—O—CH(CH₃)₂ 4.103 —CH₃ —OCH₃

4.104

4.105 —CH₂CH₂OCH₃ —SCH₄H₉(i)

4.106

—OCH₃ —OCH₃ 4.107

4.108 —C₂H₅

—OC₂H₅ 4.109 —CH₃

4.110 —CH₂CH₂Cl C₆F₅O—

4.111 —C₂H₅

—OC₂H₅ 4.112

—SCH₃ —SCH₃ 4.113

—SC₂H₅ 4.114

C₆F₅O— —OCH₃ 4.115

C₆F₅O— —SCH₃ 4.116 —CH₃

C₆F₅O— 4.117

—SCH₃ —SCH₃ 4.118 —CH₃ C₆F₅O—

4.119 —CH₂C≡CH

C₆F₅O— 4.120 —CH₂CH₂F

—OCH₂CH₂F 4.121 —C₇H₁₅(n) —SCH₃ —SCH₃ 4.122 —C₅H₁₁(n) —OC₅H₁₁(n)

4.123

—S—CH(CH₃)₂ —S—CH(CH₃)₂ 4.124

—SC₂H₅ —SC₂H₅ 4.125

—SCH₃ —SCH₃ 4.126

—S—CH(CH₃)₂ —S—CH(CH₃)₂ 4.127 —CH₂CH₂Cl

4.128 —CH₃

—OCH₂CH₂SC₂H₅ 4.129

—SCH₃ 4.130

—O—CH(CH₃)₂ —O—CH(CH₃)₂ 4.131

—SCH₃ —SCH₃ 4.132 —CH(CH₃)₂ —O—CH(CH₃)₂

4.133 —C₂H₅

—OC₂H₅ 4.134

—SCH₃ —SCH₃ 4.135

—OCH₂CF₃ —OCH₂CF₃ 4.136 —CH₃ —OCH₃

4.137

Cl —OCH₃ 4.138

Cl —S—CH(CH₃)₂ 4.139 —CH₃ —OCH₃ Cl 4.140 —CH₂C≡CH Cl

4.141 —CH₂C≡CH Cl —SC₃H₇(n) 4.142 —CH₃ Cl —SC(CH₃)₃ 4.143

Cl —OC₃H₇(n) 4.144 —CH₂CH₂F

Cl 4.145

Cl —OCH₃ 4.146

Cl —SC₂H₅ 4.147

—SCH₂CH(CH₃)C₂H₅ Cl 4.148 —CH₂CH₂Br Cl —SCH₂CH═CH₂ 4.149 —C₂H₅ Cl —OC₂H₅ 4.150 —CH₂C≡CH —SCH₂CF₃ Cl 4.151 —C₄H₉(n) Cl —OC₄H₉(n) 4.152 —C₄H₉(n) Cl —SC₄H₉(n) 4.153

—OC₂H₅ —OC₂H₅ 4.154 —CH(CH₃)₂ —SCH₂CF₃ —SCH₂CF₃ 4.155

Cl 4.156 d₃

—OC₆F₅ —OCH₂CH₂Cl 4.157 d₃ —CH₂CH₂Si(CH₃)₃ —OC₆F₅ —OCH₂CH₂Cl 4.158 d₃ —(CH₂)₃Si(CH₃)₃ —OC₆F₅ —OCH₂CH₂Cl 4.159 d₃

—OC₆F₅ —OCH₂CH₂Cl 4.160 d₃ —CH₂Si(CH₃)₃ —OC₆F₅ —OCH₂CH₂Cl 4.161 d₃ —CH₃ —OCH₃

4.162 d₃ —C₂H₅ —OC₂H₅

4.163 d₃ —CH₃ —OCH₃

4.164 d₃ —C₂H₅ —SC₆F₅ —OC₂H₅ 4.165 d₃

—OC₆F₅ —OCH₂CH₂Cl 4.166 d₃

—OCH₂CH₂Cl 4.167 d₃

—OC₆F₅ —OCH₂CH₂Cl 4.168 d₃ —OCH₂CH₂Cl —OC₆F₅ —OCH₂CH₂Cl 4.169 d₃

—OC₆F₅ —OCH₂CH₂Cl

Physical data of compounds in Table 4:

Comp. No. Physical data 4.1 ¹H-NMR: 7.4 ppm (2H); 7.25 ppm (1H); 7.15 ppm (2H); 3.9 ppm (3H); 3.5 ppm (3H) 4.2 ¹³C-NMR: 169.5 ppm; 54.7 ppm; 49.1 ppm 4.4 ¹³C-NMR: 181.8 ppm; 164.9 ppm; 65.9 ppm; 41.6 ppm; 36.5 ppm; 22.9 ppm 4.5 Melting point 75-76° C. 4.8 ¹H-NMR: 4.6 ppm (2H); 4.4 ppm (2H); 3.3 ppm (4H); 1.35 ppm (3H); 1.25 ppm (3H) 4.9 ¹H-NMR: 7.2 ppm (1H); 7.0 ppm (2H); 3.9 ppm (3H); 3.4 ppm (3H) 4.12 ¹H-NMR: 7.1 ppm (1H); 6.9 ppm (2H); 4.9 ppm (2H); 3.4 ppm (3H); 2.5 ppm (1H) 4.15 ¹H-NMR: 4.3 ppm (2H); 3.7 ppm (2H); 1.4-1.9 ppm (4H); 0.9-1.1 ppm (6H) 4.16 ¹³C-NMR: 170.0 ppm; 167.9 ppm; 136.0-143.2 ppm; 125.9 ppm; 55.2 ppm; 49.1 ppm 4.18 ¹H-NMR: 3.95 ppm (2H); 3.85 ppm (2H); 3.6 ppm (2H); 1.4 ppm (6H) 4.20 ¹H-NMR: 7.1 ppm (1H); 6.9 ppm (2H); 4.3 ppm (2H); 3.7 ppm (2H); 1.3 ppm (6H) 4.22 ¹H-NMR: 4.0 ppm (2H); 3.7 ppm (2H); 1.6 ppm (9H) 4.23 ¹³C-NMR: 160.0 ppm; 122.6 ppm; 65.1 ppm; 63.6 ppm; 41.6 ppm 4.26 ¹H-NMR: 4.3 ppm (4H); 3.6 ppm (2H); 1.8 ppm (4H); 1.6 ppm (2H); 1.0 ppm (6H); 0.9 ppm (3H) 4.29 ¹H-NMR: 5.2 ppm (4H); 4.0 ppm (2H); 3.6 ppm (2H) 4.33 ¹H-NMR: 3.95 ppm (6H); 3.7 ppm (2H); 1.3 ppm (3H) 4.38 ¹³C-NMR: 168.2 ppm; 94.3 ppm; 76.5 ppm; 64.9 ppm; 41.6 ppm 4.41 ¹H-NMR: 7.2-8.0 ppm (4H); 4.35 ppm (2H); 4.25 ppm (2H); 3.7-3.9 ppm (2H); 1.2-1.4 ppm (9H) 4.43 ¹H-NMR: 7.5 ppm (1H); 7.3 ppm (1H); 7.1 ppm (1H); 3.9 ppm (3H); 3.4 ppm (3H) 4.45 ¹³C-NMR: 168.5 ppm; 167.2 ppm; 136.1-143.0 ppm; 125.8 ppm; 81.7 ppm; 67.2 ppm; 40.7 ppm; 33.8 ppm 4.49 ¹H-NMR: 3.95 ppm (2H); 3.65 ppm (2H); 1.6 ppm (18H) 4.50 ¹H-NMR: 4.4 ppm (4H); 3.7 ppm (2H); 1.4 ppm (6H); 1.3 ppm (3H) 4.86 Melting point 141-142° C. 4.156 ¹³C-NMR: 169.0 ppm; 167.7 ppm; 142.8 ppm; 119.9 ppm; 67.3 ppm; 62.8 ppm; 45.6 ppm; 40.8 ppm; 40.6 ppm; 38.0 ppm; 36.5 ppm; 31.5 ppm; 31.3 ppm; 26.1 ppm; 21.0 ppm 4.157 ¹³C-NMR: 169.0 ppm; 167.6 ppm; 67.3 ppm; 63.7 ppm; 40.9 ppm; 18.4 ppm; −1.7 ppm 4.158 ¹H-NMR: 4.6 ppm (2H); 3.75 ppm (2H); 3.6 ppm (2H); 1.65 ppm (2H); 0.5 ppm (2H); 0.0 ppm (9H) 4.159 ¹H-NMR: 4.6 ppm (2H); 3.8 ppm (2H); 3.2 ppm (2H); 2.0 ppm (3H); 1.6-1.8 ppm (6H); 1.5 ppm (6H) 4.160 ¹H-NMR: 4.55 ppm (2H); 3.7 ppm (2H); 3.0 ppm (2H); 0.0 ppm (9H) 4.161 ¹H-NMR: 7.3-7.0 ppm (3H); 3.95 ppm (3H); 3.4 ppm (3H); 2.25 ppm (3H) 4.162 ¹H-NMR: 7.1-7.4 ppm (5H); 4.35 ppm (2H); 3.75 ppm (2H); 1.2-1.4 ppm (6H) 4.163 ¹H-NMR: 6.9-7.3 ppm (4H); 3.95 ppm (3H); 3.8 ppm (3H); 3.4 ppm (3H) 4.164 ¹H-NMR: 5.2 ppm (4H); 4.0 ppm (2H); 3.65 ppm (2H) 4.165 ¹H-NMR: 5.3 ppm (1H); 4.6 ppm (2H); 3.8 ppm (2H); 3.6 ppm (2H); 1.9-2.4 ppm (7H); 1.25 ppm (3H); 1.1 ppm (1 H); 0.8 ppm (3H) 4.166 ¹H-NMR: 7.0 ppm (1H); 4.55 ppm (1H+2H); 3.75 ppm (2H); 0.8-1.9 ppm (16H) 4.167 ¹³C-NMR: 168.8 ppm; 168.4 ppm; 167.6 ppm; 167.1 ppm; 125-143 ppm; 80.5 ppm; 80.3 ppm; 67.3 ppm; 47.5 ppm; 44.8 ppm; 41.4 ppm; 40.7 ppm; 38.4 ppm; 37.0 ppm; 33.9 ppm; 27.3 ppm; 23.8 ppm; 19.6 ppm 4.168 ¹³C-NMR: 169.0 ppm; 167.7 ppm; 125-143 ppm; 67.7 ppm; 64.7 ppm; 41.4 ppm; 40.8 ppm 4.169 ¹³C-NMR: 168.4 ppm; 167.1 ppm; 84.8 ppm; 67.3 ppm; 47.9 ppm; 41.8 ppm; 40.8 ppm; 34.5 ppm; 33.4 ppm; 32.6 ppm; 29.2 ppm; 26.0 ppm; 25.7 ppm; 23.9 ppm

Example H13 Preparation of 3-amino-1-(β-chloroethoxy)-5-(2′,4′-dichlorophenoxy)thiatriazine (process d₄)

6.5 g (0.013 mol) of 1-(β-chloroethoxy)-3,5-di(2′,4′-dichlorophenoxy)thiatriazine are dissolved in 100 ml of tetrahydrofuran. Thereafter, ammonia gas is passed in at 20° C. until the starting material can no longer be detected in a thin layer chromatogram (about 15 minutes). The reaction mixture is concentrated on a rotary evaporator and hexane is added to the still hot residue until crystallization starts. The crystals formed are filtered off with suction, washed with hexane and dried. 4.00 g (86.5% of theory) of the desired compound are obtained as crystals of melting point 141-142° C. Cl analysis: 29.3% (calculated 29.9%); ¹H-NMR (300 MHz, CDCl₃): 7.2-7.5 ppm (3H), 6.6 and 6.3 ppm (2H), 3.9 ppm (2H), 3.6 ppm (2H).

Example H14 Preparation of 3-amino-1-isopropoxy-5-(2′,5′-difluorophenoxy)thiatriazine (process g)

0.50 g (0.0084 mol) of isopropanol is reacted with 0.37 g (0.0084 mol) of 55% sodium hydride in oil in 30 ml of tetrahydrofuran. 2.60 g (0.008 mol) of 3-amino-1-(β-chloroethoxy)-5-(2′,5′-difluorophenoxy)thiatriazine are added to the resulting suspension of the sodium isopropanolate at room temperature, and a slightly exothermic reaction takes place.

Extraction of the reaction mixture with water and ethyl acetate gives 2.0 g of crude product, which is recrystallized from a mixture of ethyl acetate/hexane 3/5. Yield of desired product 1.82 g (75% of theory) of melting point 163-164° C.

Analysis: C₁₁H₁₂F₂N₄O₂S;

calculated. found [%] [%] C 43.7 43.3 H  4.0  4.0 N 18.5 18.4

¹H-NMR (300 MHz, CDCl₃): 6.8-7.2 ppm (3H); 5.1-5.5 ppm (1H); 4.4 ppm (1H); 1.3 ppm (6H).

Example H15 Preparation of 3-dimethylamino-1-(β-chloroethoxy)-5-(2′-carboethoxyphenoxy)thiatriazine (process c₄)

2.22 g (0.0064 mol) of 3-chloro-1-(β-chloroethoxy)-5-(2′-carboethoxyphenoxy)thiatriazine are dissolved in 30 ml of tetrahydrofuran. Dimethylamine is passed in at 0° C. until the conversion is complete, the reaction mixture is extracted with water and ethyl acetate, the extract is concentrated and the crude product is purified by means of chromatography (silica gel; ethyl acetate/hexane mixture). The desired product is obtained as an oil in a yield of 1.40 g (57% of theory). The ¹H-NMR spectrum is in agreement with the structure of the desired compound; mass spectrum: [M⁺]386.

Example H16 Preparation of 3-amino-5-(2,5-difluorophenoxy)-1-(3-hexyloxy)thiatriazine

2.1 g of trimethylamine solution (40% in water) are added to a mixture of 3.6 g of 3-amino-5-chloro-1-(3-hexyloxy)thiatriazine (0.014 mol), 70 ml of methylene chloride and 2.05 g of 2,5-difluorophenol (0.01 6 mol). The reaction mixture is stirred at 20° C. until the conversion is complete, and is then evaporated. Water is added to the resulting residue and the residue is filtered off with suction. The resulting solid is stirred in diethyl ether and filtered off, the clear ether solution is concentrated and pentane is added to the residue. The desired product precipitates in the form of white crystals of melting point 171-172° C.

The compounds listed in the following Table 5 can be prepared analogously to Examples H13 to H16.

TABLE 5 Compounds of the formula III (III)

Comp. No. Process R₇ R₃ R₂ 5.1 d₄ —CH₂CH₂Cl C₆H₅O— —NH₂ 5.2 d₄ —CH₂CH₂C₆H₅

—N(CH₃)C₄H₉(n) 5.3 q —CH(CH₃)₂

—NH₂ 5.4 d₄ —CH₂CH₂Cl

—NH₂ 5.5 d₅ —CH₂CH₂Cl

—NH₂ 5.6 d₄ —CH₂CH₂Cl C₆F₅O— —N(CH₃)₂ 5.7 q

—NH₂ 5.8 q

—NH₂ 5.9

C₆F₅O— —NH₂ 5.10 d₄ —CH₂CH₂C₆H₅

5.11 d₄ —CH₂CH₂Cl C₆H₅O— —N(CH₃)₂ 5.12

C₆F₅O— —NH₂ 5.13 d₄ —CH₂CH₂Cl C₆F₅O— —NH₂ 5.14 q

—NH₂ 5.15 d₄ —CH₂CH₂Cl

—NHC(CH₃)₃ 5.16

C₆F₅O— —NH₂ 5.17 d₄ —CH₂CH₂Cl

5.18

C₆F₅O— —NH₂ 5.19 q

—NH₂ 5.20 —CH₂CH₂Cl

—NH₂ 5.21

—NH₂ 5.22 c₄ —CH₂CH₂Cl

—N(CH₃)₂ 5.23 d₄ —CH₂CH₂Cl

—N(CH₃)₂ 5.24 —CH₂CH₂Cl

—NH₂ 5.25

—NH₂ 5.26

C₆F₅O— —NH₂ 5.27

C₆F₅O— —NH₂ 5.28 d₄ —CH₂CH₂Cl

—NH₂ 5.29 —CH₂CH₂Cl

5.30 q

C₆F₅O— —NH₂ 5.31 d₄

—NH₂ 5.32 —CH₂CH₂Cl

—NH₂ 5.33 —CH₂CH═CH₂ C₆F₅O— —NH₂ 5.34

C₆F₅O— —NH₂ 5.35 d₄

5.36 —(CH₂)₆CH₃ C₆F₅O— —NH₂ 5.37

—NH₂ 5.38 d₄

C₆F₅O— —NH₂ 5.39

—NH₂ 5.40 —CH₂CH₂NO₂

—NH₂ 5.41 —CH₂C₆F₅

—NH₂ 5.42 d₄

—NH₂ 5.43

—NH₂ 5.44

—NH₂ 5.45 q —CH₃

—NHCH₂CH₂CH₃ 5.46 q

C₆F₅O— —NH₂ 5.47 q

C₆F₅O— —NH₂ 5.48 d₄ —CH₂CH₂Cl

—NH₂ 5.49 —CH₂CH₂Cl C₆F₅O—

5.50

—NH₂ 5.51 q —CH₃

—N(CH₃)₂ 5.52 q

C₆F₅O— —NH₂ 5.53

C₆F₆O— —NH₂ 5.54 q —CH₃

—NH₂ 5.55 d₄ —CH₂CH₂Cl

—N(CH₃)₂ 5.56

C₆F₅O— —NH₂ 5.57

C₆F₅O— —NH₂ 5.58 q

—NH₂ 5.59 q

C₆F₅O— —NH₂ 5.60 d₄ —CH₂CH₂Cl

—NHCH₂CH₂CH₃ 5.61

C₆F₅O— —NH₂ 5.62

C₆F₅O— —NH₂ 5.63

C₆F₅O— —NH₂ 5.64 q —CH₃

—NHCH₂CH₂CH₃ 5.65 q

C₆F₅O— —NH₂ 5.66 —CH₂CH₂COOC₂H₅ C₆F₅O— —NH₂ 5.67 d₄

—NH₂ 5.68 —CH₂C═CH C₆F₅O— —NH₂ 5.69

C₆F₅O— —NH₂ 5.70

C₆F₅O— —NH₂ 5.71 q —CH₃

—NH₂ 5.72 d₄

—NH₂ 5.73 c₄

—NH₂ 5.74 d₄

—NHCH₃ 5.75 q

—NH₂ 5.76

C₆F₅O— —NH₂ 5.77 —CH₂CH₂CCl₃ C₆F₅O— —NH₂ 5.78 q

C₆F₅O— —NH₂ 5.79

C₆F₅O— —NH₂ 5.80

C₆F₅O— —NH₂ 5.81

—NH₂ 5.82

C₆F₅O— —NH₂ 5.83 q

C₆F₅O— —NH₂ 5.84 q

C₆F₅O— —NH₂ 5.85 —CH₂-Adamantyl C₆F₅O— —NH₂ 5.86 q

—C₆F₅O— —NH₂ 5.87

C₆F₅S— —NH₂ 5.88 d₄

C₆F₅S— —NH₂ 5.89 d₄ —CH₂CH₂Cl C₆F₅S— —NH₂ 5.90 q

C₆F₅O— —NH₂ 5.91

C₆F₅O— —NH₂ 5.92 q

C₆F₅O— —NH₂ 5.93

C₆F₅O— —NH₂ 5.94 c₄

5.95

C₆F₅O— —NH₂ 5.96 q —CH₂CH₂OCH₃

—NH₂ 5.97

—NHC₄H₉(n) 5.98 d₄

C₆F₅O— —NH₂ 5.99

C₆F₅O— —NH₂ 5.100

C₆F₅S— —NH₂ 5.101

C₆F₅O— —NH₂ 5.102 q —CH₂CH₂F

—NH₂ 5.103 q

—NH₂ 5.104

C₆F₅O— —NH₂ 5.105 —(CH₂)₇CH₃

—NHCH₃ 5.106

C₆F₅O— —NH₂ 5.107 q —C₂H₅

—NH₂ 5.108 q

—NH₂ 5.109 —CH(CH₃)C₂H₅

—NH₂ 5.110 q —C(CH₃)₃

—NH₂ 5.111

C₆F₅O— —NH₂ 5.112

C₆F₅O— —NH₂ 5.113 q —CH₃

—NHC(CH₃)₃ 5.114

C₆F₅O— —NH₂ 5.115

C₆F₅O— —NH₂ 5.116 q

—NH₂ 5.117

C₆F₅O— —NH₂ 5.118

C₆F₅O— —NH₂ 5.119 q —CH₃

—NH₂ 5.120 q

C₆F₅O— —NH₂ 5.121 d₄

—NHCH(CH₃)CH₂OCH₃ 5.122 d₄

—NH₂ 5.123

C₆F₅O— —NH₂ 5.124

C₆F₅O— —NH₂ 5.125 q —C₂H₅

—NH₂ 5.126 d₄

—NH₂ 5.127

C₆F₅O— —NH₂ 5.128

C₆F₅O— —NH₂ 5.129 q

—NH₂ 5.130 q

—NH₂ 5.131 q

C₆F₅O— —NH₂ 5.132 d₄

C₆F₅O— —NH₂ 5.133 d₄

—NH₂ 5.134

C₆F₅O— —NH₂ 5.135 q

C₆F₅O— —NH₂ 5.136

C₆F₅O— —NH₂ 5.137

C₆F₅O— —NH₂ 5.138 d₄

—NHCH₃ 5.139

C₆F₅O— —NH₂ 5.140

C₆F₅O— —NH₃ 5.141 q

C₆F₅O— —NH₂ 5.142

C₆F₅O— —NH₂ 5.143 q

—NH₂ 5.144 d₄

—NH₂ 5.145 q

C₆F₅O— —NH₂ 5.146 q

C₆F₅O— —NH₂ 5.147 d₄

—NH₂ 5.148 q

C₆F₅O— —NH₂ 5.149

—NH₂ 5.150 d₄

C₆F₅S— —NH₂ 5.151 d₄

C₆F₅O— —NHC₂H₅ 5.152 d₄

C₆F₅O— —NH₂ 5.153 d₄

C₆F₅O— —NH₂ 5.154 q

C₆F₅O— —NH₂ 5.155

C₆F₅O— —NH₂ 5.156 q —(CH₂)₄CH₃

—NH₂ 5.157 q

—NH₂ 5.158

C₆F₅O— —NH₂ 5.159

—NH₂ 5.160 q —CH₂CH₂SC₂H₅

—NH₂ 5.161 d₄ —CH₂CH₂Si(CH₃)₃ C₆F₅O— —NH₂ 5.162 q —(CH₂)₉CH₃

—NH₂ 5.163

C₆F₅O— —NH₂ 5.164

C₆F₅O— —NH₂ 5.165

C₆F₅O— —NH₂ 5.166

C₆F₅O— —NH₂ 5.167 —CH₂CH₂Cl

—NH₂ 5.168 q —(CH₂)₂(CF₂)₃CF₃

—NH₂ 5.169

C₆F₅O— —NH₂ 5.170 —CH₂CH(C₆H₅)₂ C₆F₅O— —NH₂ 5.171

C₆F₅O— —NH₂ 5.172 q

—NH₂ 5.173

C₆F₅O— —NH₂ 5.174 d₄ —CH₂CH₂Cl

—NH₂ 5.175

C₆F₅O— —NH₂ 5.176 q

C₆F₅O— —NH₂ 5.177 d₄ —CH₂CH₂Cl

—NH₂ 5.178 d₄ —CH₂CH₂Cl

—NHCH₂CH₂CH₃ 5.179

—NHC₄H₉(n) 5.180 d₄

C₆F₅O— —NH₂ 5.181

C₆F₅O— —NH₂ 5.182 d₄ —CH₂CH₂Cl

—NHCH(CH₃)₂ 5.183 d₄ —CH₂CH₂Cl

—N(C₂H₅)₂ 5.184 d₄ —CH₂CH₂Cl

—NH₂ 5.185

C₆F₅O— —NH₂ 5.186

C₆F₅O— —NH₂ 5.187

C₆F₅O— —NH₂ 5.188 d₄ —CH₂CH₂Cl

5.189 —CH₂CH₂Cl

—NH₂ 5.190 —CH₂CH₂Cl

—NH₂ 5.191

C₆F₅O— —NH₂ 5.192 d₄ —CH₂CH₂Cl

—NH₂ 5.193 d₄ —CH₂CH₂Cl

—N(CH₃)₂ 5.194

C₆F₅O— —NH₂ 5.195 q

C₆F₅O— —NH₂ 5.196

C₆F₅O— —NH₂ 5.197 q

C₆F₅O— —NH₂ 5.198

C₆F₅O— —NH₂ 5.199 —CH₂CH₂Cl

—NH₂ 5.200 —CH₂CH₂Cl

—NH₂ 5.201

C₆F₅O— —NH₂ 5.202

C₆F₅O— —NH₂ 5.203 —CH₂CH₂Cl

—NH₂ 5.204

—NH₂ 5.205

—NH₂ 5.206 —CH₂CH₂Cl

—NH₂ 5.207

C₆F₅O— —NH₂ 5.208

—NH₂ 5.209

—NH₂ 5.210 —CH₂CH₂Cl

—NH₂ 5.211 —CH₂CH₂Cl

—NH₂ 5.212 —CH₂CH₂Cl

—NH₂ 5.213

—NH₂ 5.214

—NH₂ 5.215 —CH₂CH₂Cl

—NH₂ 5.216 —CH₂CH₂Cl

—NH₂ 5.217 —CH₂CH₂Cl

—NH₂ 5.218 —CH₂CH₂Cl

—NH₂ 5.219

—NH₂ 5.220 —CH₂CH₂Cl

—NH₂ 5.221 —CH₂CH₂Cl

—NH₂ 5.222 —CH₂CH₂Cl

—NH₂ 5.223 —CH₂CH₂Cl

—NH₂ 5.224 —CH₂CH₂Cl

—NH₂ 5.225

—NH₂ 5.226 —CH₂CH₂Cl

—NH₂ 5.227

—NH₂ 5.228 —CH₂CH₂Cl

—NH₂ 5.229 —CH₂CH₂Cl

—NH₂ 5.230 —CH₂CH₂Cl

—NH₂ 5.231 —CH₂CH₂Cl

—NH₂ 5.232 —CH₂CH₂Cl

—NH₂ 5.233 —CH₂CH₂Cl

—NH₂ 5.234 —CH₂CH₂Cl

—NH₂ 5.235 —CH₂CH₂Cl

—NH₂ 5.236 —CH₂CH₂Cl

—NH₂ 5.237

—NH₂ 5.238

—NH₂ 5.239 —CH₂CH₂Cl

—NH₂ 5.240 —CH₂CH₂Cl

—NH₂ 5.241

—NH₂ 5.242 —CH₂CH₂Cl

—NH₂ 5.243 —CH₂CH₂Cl

—NH₂ 5.244 —CH₂CH₂Cl

—NH₂ 5.245 —CH₂CH₂Cl

—NH₂ 5.246 —CH₂CH₂Cl

—NH₂ 5.247 —CH₂CH₂Cl

—NH₂ 5.248 —CH₂CH₂Cl

—NH₂ 5.249 —CH₂CH₂Cl

—NH₂ 5.250 —CH₂CH₂Cl

—NH₂ 5.251 —CH₂CH₂Cl

—NH₂ 5.252 —CH₂CH₂Cl

—NH₂ 5.253 —CH₂CH₂Cl

—NH₂ 5.254 —CH₂CH₂Cl

—NH₂ 5.255 —CH₂CH₂Cl

—NH₂ 5.256 —CH₂CH₂Cl

—NH₂ 5.257 —CH₂CH₂Cl

—NH₂ 5.258 —CH₂CH₂Cl

—NH₂ 5.259 —CH₂CH₂Cl

—NH₂ 5.260 —CH₂CH₂Cl

—NH₂ 5.261 —CH₂CH₂Cl

—NH₂ 5.262 —CH₂CH₂Cl

—NH₂ 5.263 —CH₂CH₂Cl

—NH₂ 5.264 —CH₂CH₂Cl

—NH₂ 5.265 —CH₂CH₂Cl

—NH₂ 5.266 —CH₂CH₂Cl

—NH₂ 5.267 —CH₂CH₂Cl

—NH₂ 5.268 —CH₂CH₂Cl

—NH₂ 5.269 —CH₂CH₂Cl

—NH₂ 5.270 —CH₂CH₂Cl

—NH₂ 5.271 —CH₂CH₂Cl

—NH₂ 5.272 —CH₂CH₂Cl

—NH₂ 5.273 —CH₂CH₂Cl

—NH₂ 5.274 —CH₂CH₂Cl

—NH₂ 5.275 —CH₂CH₂Cl

—NH₂ 5.276 —CH₂CH₂Cl

—NH₂ 5.277 —CH₂CH₂Cl

—NH₂ 5.278 —CH₂CH₂Cl

—NH₂ 5.279 —CH₂CH₂Cl

—NH₂ 5.280 —CH₂CH₂Cl

—NH₂ 5.281 —CH₂CH₂Cl

—NH₂ 5.282 —CH₂CH₂Cl

—NH₂ 5.283 —CH₂CH₂Cl

—NH₂ 5.284 —CH₂CH₂Cl

—NH₂ 5.285 —CH₂CH₂Cl

—NH₂ 5.286

C₆F₅O— —NH₂ 5.287

C₆F₅O— —NH₂ 5.288

C₆F₅O— —NH₂ 5.289

C₆F₅O— —NH₂ 5.290

C₆F₅O— —NH₂ 5.291

C₆F₅O— —NH₂ 5.292

C₆F₅O— —NH₂ 5.293

C₆F₅O— —NH₂ 5.294

C₆F₅O— —NH₂ 5.295

C₆F₅O— —NH₂ 5.296

C₆F₅O— —NH₂ 5.297

C₆F₅O— —NH₂ 5.298

C₆F₅O— —NH₂ 5.299

C₆F₅O— —NH₂ 5.300

C₆F₅O— —NH₂ 5.301

C₆F₅O— —NH₂ 5.302

C₆F₅O— —NH₂ 5.303

C₆F₅O— —NH₂ 5.304

C₆F₅O— —NH₂ 5.305

C₆F₅O— —NH₂ 5.306

C₆F₅O— —NH₂ 5.307

C₆F₅O— —NH₂ 5.308

C₆F₅O— —NH₂ 5.309

C₆F₅O— —NH₂ 5.310

C₆F₅O— —NH₂ 5.311

C₆F₅O— —NH₂ 5.312

C₆F₅O— —NH₂ 5.313

C₆F₅O— —NH₂ 5.314

C₆F₅O— —NH₂ 5.315 d₄ —(CH₂)₃Si(CH₃)₃ C₆F₅O— —NH₂ 5.316 d₄

C₆F₅O— —NH₂ 5.317 c₅

C₆F₅O— —NH₂ 5.318 c₅

—NH₂ 5.319 d₄

C₆F₅O— —NH₂ 5.320 d₄

C₆F₅O— —NH₂ 5.321 d₄ —CH₂Si(CH₃)₃ C₆F₅O— —NH₂ 5.322 d₄

C₆F₅O— —NHC₂H₅ 5.323 d₄

C₆F₅O— —NHCH₃ 5.324 d₄

C₆F₅O— —NH₂ 5.325 d₄

C₆F₅O— —NH₂ 5.326 d₄

C₆F₅O— —NH₂ 5.327 d₄

C₆F₅O— —NH₂ 5.328 d₄

C₆F₅O— —NH₂ 5.329 d₄ —CH(CH₃)—Si(CH₃)₃ C₆F₅O— —NH₂ 5.330 q —CH₃ C₆F₅O— —NH₂ 5.331 —CH(CH₃)COOCH₃ C₆F₅O— —NH₂ 5.332 c₅

C₆F₅O— —NH₂ 5.333 d₄ —CH₂CH₂Cl

—NH₂ 5.334

—NH₂ 5.335 q —CH₂CH₂Cl CF₃CH₂O— —NH₂ 5.336 q —CH₂CH₂Cl (CF₃)₂CHO— —NH₂ 5.337 q —CH₂CH₂Cl CF₃CCl₂CH₂O— —NH₂ 5.338 d₄

—NH₂ 5.339 c₅ —CH[CH₂CH(CH₃)₂]₂ C₆F₅O— —NH₂ 5.340 c₅

—NH₂ 5.341 d₄

—NH₂ 5.342 d₄

—NH₂ 5.343 d₄ —CH₂Si(CH₃)₃

—NH₂ 5.344 d₄

C₆F₅O— —NH₂ 5.345 d₄

C₆F₅O— —NH₂ 5.346 d₄

C₆F₅O— —NH₂ 5.347

C₆F₅O— —NH₂ 5.348

C₆F₅O— —NH₂ 5.349 d₄

C₆F₅O— —NH₂ 5.350 d₄

C₆F₅O— —NH₂ 5.351 d₄

C₆F₅O— —NH₂ 5.352 d₄

C₆F₅O— —NH₂ 5.353

C₆F₅O— —NH₂ 5.354

C₆F₅O— —NH₂ 5.355 d₄

C₆F₅O— —NH₂ 5.356 d₄

C₆F₅O— —NH₂ 5.357 d₄

C₆F₅O— —NH₂ 5.358 d₄

C₆F₅O— —NH₂ 5.359 d₄

C₆F₅O— —NH₂ 5.360 d₄

C₆F₅O— —NH₂ 5.361

C₆F₅O— —NH₂ 5.362

C₆F₅O— —NH₂ 5.363 d₄

C₆F₅O— —NH₂ 5.364 d₄

C₆F₅O— —NH₂ 5.365

C₆F₅O— —NH₂ 5.366 d₄ —CH₂CH₂Cl

—NH₂ 5.367

C₆F₅O— —NH₂ 5.368

C₆F₅O— —NH₂ 5.369 d₄

C₆F₅O— —NH₂ 5.370 —CH₂CH₂C₆F₅ C₆F₅O— —NH₂ 5.371

C₆F₅O— —NH₂ 5.372

C₆F₅O— —NH₂ 5.373

C₆F₅O— —NH₂ 5.374

C₆F₅O— —NH₂ 5.375 d₄

—NH₂ 5.376 d₄

—NH₂ 5.377 d₄

—NH₂

Physical data of compounds in Table 5:

Comp. No. Physical data 5.1 Melting point 152-153° C. 5.2 ¹H-NMR: 6.8-7.3 ppm (8H); 3.7-4.0 ppm (2H); 3.2-3.6 ppm (2H); 2.8-3.0 ppm (5H); 0.8-1.6 ppm (7H) 5.3 Melting point 163-164° C. 5.4 Melting point 167-168° C. 5.5 Melting point 141-142° C. 5.6 ¹H-NMR: 3.8-4.0 ppm (2H); 3.6 ppm (2H); 3.2 ppm (3H); 3.0 ppm (3H) 5.7 Melting point 145-146° C. 5.8 Melting point 148-149° C. 5.10 ¹H-NMR: 6.8-7.3 ppm (8H); 5.3-5.5 ppm (1H); 4.0-4.3 ppm (1H); 3.8 ppm (2H); 2.9 ppm (2H) 5.11 ¹H-NMR: 7.1-7.4 ppm (5H); 3.9 ppm (2H); 3.6 ppm (2H); 3.13 ppm (3H); 3.05 ppm (3H) 5.13 Melting point 127-128° C. 5.14 Melting point 140-141° C. 5.15 ¹H-NMR: 6.5-7.2 ppm (3H); 5.3 ppm (1H); 3.6-4.0 ppm (4H); 1.45 ppm (9H) 5.17 ¹H-NMR: 7.1-7.5 ppm (3H); 3.6-4.0 ppm (12H) 5.19 Melting point 179-180° C. 5.22 ¹H-NMR: 7.2-8.0 ppm (4H); 4.3 ppm (2H); 3.8-4.1 ppm (2H); 3.6 ppm (2H); 3.1 ppm (3H); 3.0 ppm (3H); 1.3 ppm (3H) 5.23 ¹H-NMR: 6.9-7.2 ppm (3H); 3.8-4.0 ppm (2H); 3.6 ppm (2H); 3.15 ppm (3H); 3.0 ppm (3H) 5.28 Melting point 130-131° C. 5.30 Melting point 207-208° C. 5.31 Melting point 159-160° C. (decomposition) 5.35 ¹H-NMR: 6.8-7.4 ppm (8H); 5.5 ppm (1H); 4.7 ppm (2H); 4.2 ppm (1H); 1.9 ppm (4H); 1.4-1.7 ppm (4H) 5.38 Melting point 163-164° C. 5.42 Melting point 181-182° C. 5.45 Melting point 98-99° C. 5.46 Melting point 147-148° C. 5.47 Melting point 125-126° C. 5.48 Melting point 161-162° C. 5.51 Melting point 87-88° C. 5.52 Melting point 138-139° C. 5.54 Melting point 215-216° C. 5.55 ¹H-NMR: 6.8-7.1 ppm (3H); 3.8-4.0 ppm (2H); 3.6 ppm (2H); 3.15 ppm (3H); 3.0 ppm (3H) 5.58 Melting point 202-203° C. 5.59 Melting point 123-124° C. 5.60 ¹H-NMR: 6.9-7.2 ppm (3H); 3.7-4.0 ppm (2H); 3.6 ppm (2H); 3.4 ppm (2H); 1.6 ppm (2H); 0.9 ppm (3H) 5.64 Melting point 112-113° C. 5.65 Melting point 103-104° C. 5.67 Melting point 176-177° C. 5.71 Melting point 204-206° C. (decomposition) 5.72 Melting point 178-179° C. 5.73 Melting point 173-174° C. 5.74 ¹H-NMR: 6.8-7.3 ppm (4H); 4.3 ppm (1H); 4.0 ppm (1H); 3.8 ppm (3H); 2.8-3.0 ppm (3H); 1.2-2.2 ppm (12H) 5.75 Melting point 167-168° C. 5.76 Melting point 175-176° C. (decomposition) 5.78 Melting point 165-166° C. 5.83 Oil 5.84 Melting point 109-110° C. 5.85 Melting point 175-176° C. (decomposition) 5.86 Melting point 165-166° C. 5.88 Melting point 115-116° C. 5.89 Melting point 91-92° C. 5.90 Melting point 179-180° C. (decomposition) 5.92 Melting point 212-213° C. 5.94 ¹H-NMR: 6.9-7.3 ppm (4H); 3.8-4.6 ppm (6H); 3.8 ppm (3H); 0.7-2.9 ppm (22H) 5.96 Melting point 108-109° C. 5.98 Melting point 138-139° C. 5.101 Melting point 182-183° C. 5.102 Melting point 145-146° C. 5.103 Melting point 183-185° C. 5.107 Melting point 190-191° C. 5.108 Melting point 204-205° C. 5.110 Melting point 124-125° C. 5.113 ¹H-NMR: 6.5-7.2 ppm (3H); 5.3 ppm (1H); 3.4 ppm (3H); 1.45 ppm (9H) 5.114 Melting point 137-138° C. 5.116 Melting point 216-217° C. 5.117 Melting point 161-162° C. 5.119 Melting point 194-196° C. (decomposition) 5.120 Melting point 156-157° C. 5.121 ¹H-NMR: 7.3 ppm (5H); 7.1 ppm (1H); 6.9 ppm (2H); 5.6 ppm (1H); 4.7 ppm (2H); 4.2 ppm (1H); 3.2-3.4 ppm (5H); 1.2 ppm (3H) 5.122 Melting point 103-104° C. 5.125 Melting point 162-163° C. 5.126 Melting point 197-198° C. 5.127 Melting point 118-119° C. 5.129 Melting point 140-141° C. 5.130 Melting point 167-168° C. 5.131 Melting point 140-141° C. 5.132 Melting point 147-148° C. 5.133 Melting point 139-140° C. 5.135 ¹³C-NMR: 166.0 ppm; 165.2 ppm; 75.6 ppm; 68.5 ppm; 66.2 ppm; 27.8 ppm; 25.6 ppm; 22.9 ppm 5.138 Melting point 132-133° C. 5.141 Melting point 115-116° C. 5.143 Melting point 105-106° C. 5.144 Melting point 183-184° C. 5.145 Melting point 106-107° C. 5.146 Melting point 182-184° C. 5.147 Melting point 198-199° C. 5.148 Melting point 108-109° C. 5.150 Melting point 115-116° C. 5.151 Melting point 122-123° C. 5.152 Melting point 122-123° C. 5.153 Oil 5.154 Melting point 178-180° C. (decomposition) 5.156 Melting point 148-149° C. 5.157 Melting point 162-163° C. 5.160 Melting point 103-104° C. 5.161 Melting point 120-121° C. 5.162 Melting point 117-118° C. 5.168 Melting point 127-128° C. 5.172 Melting point 148-149° C. 5.174 Melting point 125-126° C. 5.176 Melting point 139-140° C. 5.177 ¹H-NMR: 8.3 ppm (1H); 7.4 ppm (1H); 7.2 ppm (1H); 6.8 ppm (1H); 6.5 ppm (1H); 3.9 ppm (2H); 3.6 ppm (2H); 2.5 ppm (3H) 5.178 ¹H-NMR: 7.1-7.4 ppm (3H); 3.8-4.0 ppm (2H); 3.6 ppm (2H); 3.3 ppm (2H); 1.4-1.7 ppm (2H); 0.8-1.0 ppm (3H) 5.180 Melting point 123-124° C. 5.182 Melting point 138-140° C. 5.183 ¹H-NMR: 7.7 ppm (1H); 7.1-7.3 ppm (2H); 5.5 ppm (1H); 3.6-4.2 ppm (4H); 3.5 ppm (2H); 3.2 ppm (2H); 1.6 ppm (3H); 1.2 ppm (3H); 0.9 ppm (3H) 5.184 Melting point 146-147° C. 5.188 Melting point 123-124° C. 5.192 Melting point 182-183° C. 5.193 ¹H-NMR: 7.7 ppm (1H); 7.2-7.3 ppm (2H); 5.5 ppm (1H); 3.6-4.2 ppm (4H); 3.1 ppm (3H); 2.9 ppm (3H); 1.6 ppm (3H) 5.195 Melting point 167-168° C. 5.197 Melting point 177-178° C. 5.207 Melting point 157-158° C. 5.315 Melting point 111-112° C. 5.316 Melting point 145-146° C. 5.317 Melting point 137-139° C. 5.318 Melting point 171-173° C. 5.319 Melting point 146-147° C. (decomposition) 5.320 Melting point 175-176° C. (decomposition) 5.321 Melting point 179-180° C. 5.322 Melting point 210-211° C. (decomposition) 5.323 solid 5.324 Melting point 112° C. (decomposition) 5.325 Melting point 116° C. (decomposition) 5.326 Melting point 118-119° C. 5.327 Melting point 148-149° C. 5.328 Melting point 129-130° C. (decomposition) 5.329 Melting point 157-158° C. (decomposition) 5.330 Melting point 142-143° C. 5.332 Melting point 142-143° C. 5.333 Melting point 141-142° C. 5.334 Melting point 124-125° C. 5.335 Melting point 137-140° C. 5.336 Resin; MS: [M⁺] 360/362 5.337 Melting point 162-163° C. 5.338 Melting point 181-182° C. 5.339 Melting point 112-114° C. 5.340 Melting point 171-172° C. 5.341 Melting point 154-155° C. 5.342 Melting point 178-179° C. 5.343 Melting point 223-224° C. 5.344 Melting point 163-164° C. 5.345 Melting point 167-168° C. 5.346 Melting point 117-118° C. 5.349 Melting point 151-152° C. 5.350 Melting point 146-147° C. 5.351 Melting point 124-125° C. 5.352 Melting point 134-135° C. 5.355 Melting point 164-165° C. 5.356 Melting point 145-146° C. 5.357 Melting point 186-187° C. 5.358 Melting point 169-170° C. 5.359 Melting point 164-165° C. 5.360 Melting point 136-137° C. 5.363 Melting point 183-184° C. 5.364 Melting point 118-119° C. 5.366 Melting point 131-132° C. (decomposition) 5.369 Melting point 146-147° C. 5.375 Melting point 188-189° C. 5.376 Melting point >225° C. 5.377 Melting point 156-157° C.

Example H17 Preparation of 3-amino-1-dipropylamino-5-(2′,5′-difluorophenoxy)thiatriazine

1.60 g (0.005 mol) of 3-amino-1-(β-chloroethoxy)-5-(2′,5′-difluorophenoxy)thiatriazine are stirred in 20 ml of toluene with 0.53 9 (0.00525 mol) of dipropylamine at 70° C. for 3.5 hours. After the reaction mixture has cooled, it is extracted with ethyl acetate and water. On concentration of the reaction mixture on a rotary evaporator, the desired product crystallizes out. It is filtered off with suction, washed and dried. Yield 1.42 g (83% of theory); melting point 184-185° C.

Analysis: C₁₄H₁₉F₂N₅OS;

calculated found [%] [%] C 48.97 48.92 H  5.58  5.61 N 20.39 20.24

Example H18 Preparation of 3-amino-1-decahydroquinolinyl-5-(2′,6′-difluorophenoxy)thiatriazine

1.00 g (0.0027 mol) of 1-(trans-2′-chlorocyclohexanolyl)-3-amino-5-(2′,6′-difluorophenoxy)thiatriazine is heated at 80-90° C. with 0.49 g (0.0035 mol of decahydroquinoline (cis/trans mixture) in 20 ml of toluene until the conversion is complete. Thereafter, the mixture is concentrated on a rotary evaporator, the residue is dissolved in ethyl acetate, the clouding formed is filtered off with suction and the filtrate is concentrated. Recrystallization of the resulting residue from a mixture of ethyl acetate/hexane gives 0.85 g (82% of theory) of the desired product of melting point 194-195° C. (decomposition). The ¹H— and ¹³C-NMR spectra are in agreement with the structure of the desired product.

Example H19 Preparation of 3-amino-5-pentafluorophenoxy-1-(piperidin-1-yl)thiatriazine

8.3 ml of 2N sodium hydroxide solution (0.0166 mol) and 2.2 g of trimethylamine solution (40% in water) (0.015 mol) are added to a mixture of 3.5 9 of 3-amino-5-chloro-1-(piperidin-1-yl)thiatriazine (0.015 mol) and 3.0 g of pentafluorophenol (0.0165 mol) in 100 ml of methylene chloride. After the mixture has been stirred for 20 hours, the organic phase is dried over sodium sulfate and filtered over silica gel, with subsequent elution with a 50/50 hexane/ethyl acetate mixture. After the collected fractions have been evaporated and the residue has been stirred in pentane, the desired product is isolated as slightly yellowish crystals of melting point 104-105° C. (decomposition).

The compounds listed in the following Table 6 can be prepared analogously to Examples H17 to H19.

TABLE 6 Compounds of the formula II (II)

Comp. No. R₁ R₃ R₂ Physical data 6.1 —NHCH₂CH₂CH₃

—NH₂ Melting point 132-133° C. 6.2

—N(CH₃)₂ ¹H-NMR: 6.8- 7.1 ppm (3H); 5.6-5.8 ppm (2H); 3.0-5.5 ppm (10 H); 2.2 ppm (2H) 6.3

—NH₂ Melting point 194-195° C. (decom- position) 6.4

—NH₂ Melting point 121-122° C. 6.5

—NH₂ Melting point 170-171° C. 6.6

C₆F₅O— —NH₂ ¹³C-NMR: 165.7 ppm; 165.0 ppm; 63.7 ppm; 44.8 ppm; 43.3 ppm; 34.1 ppm; 32.2 ppm; 31.5 ppm; 24.5 ppm. 6.7

C₆F₅O— —NH₂ Melting point 201-202° C. 6.8

C₆F₅O— —NH₂ Melting point 162-163° C. 6.9

C₆F₅O— —NH₂ Melting point 147-148° C. (decom- position) 6.10

C₆F₅O— —NH₂ ¹³C-NMR: 165.7 ppm. 165.0 ppm; 63.7 ppm. 45.1 ppm; 43.6 ppm; 34.4 ppm; 32.1 ppm; 31.6 ppm; 24.7 ppm 6.11

—NH₂ Melting point 167-168° C. 6.12

—NH₂ Melting point 148-149° C. 6.13

C₆F₅S— —NH₂ 6.14

C₆F₅O— —NH₂ Melting point 185-186° C. (decom- position) 6.15

C₆F₅O— —NH₂ Melting point 102-103° C. 6.16 —N(CH₂CH₂CN)₂ C₆F₅O— —NH₂ ¹³C-NMR: 165.8 ppm; 164.7 ppm; 118.5 ppm; 117.4 ppm; 49.6 ppm; 43.0 ppm; 18.6 ppm; 17.4 ppm 6.17 —NHC₆H₁₁(c) C₆F₅O— —NH₂ Melting point 136-137° C. 6.18

—NH₂ Melting point 189-190° C. (decom- position) 6.19

—NH₂ 6.20

—NH₂ 6.21 —N(n-C₃H₇)₂ C₆F₅O— —NH₂ Melting point 111-112° C. 6.22

C₆F₅O— —NH₂ Melting point 137-138° C. 6.23

—NH₂ Melting point 190-191° C. 6.24

C₆F₅O— —NH₂ 6.25

C₆F₅O— —NH₂ 6.26

C₆F₅O— —NH₂ 6.27

C₆F₅O— —NH₂ Melting point 150-151° C. (decom- position) 6.28

—NH₂ Melting point 137-139° C. 6.29

—NH₂ Melting point 128-129° C. 6.30

C₆F₅O— —NH₂ Melting point 161-162° C. 6.31

C₆F₅O— —NH₂ Melting point 173-174° C. 6.32

C₆F₅O— —NH₂ 6.33

—NH₂ 6.34

C₆F₅O— —NH₂ Melting point 180-181° C. (decom- position) 6.35

—NH₂ 6.36 —N[CH(CH₃)₂]₂

—NH₂ 6.37

C₆F₅O— —NH₂ Melting point 183-184° C. (decom- position) 6.38 —N(C₂H₅)₂

—NH₂ 6.39 —N(C₂H₅)C₄H₉(n)

—NHCH₃ 6.40

—NH₂ Melting point 208-209° C. 6.41

C₆F₅O— —NH₂ Melting point 162-163° C. 6.42

C₆F₅O— —NH₂ MS: [M⁺+ H, 45%] 450. [M⁺, 40% ]449 6.43 —N(CH₃)₂

—NHC₃H₆(n) 6.44

—NHCH(CH₃)₃ 6.45

—NH₂ Melting point 159-160° C. 6.46

C₆F₅O— —NH₂ Melting point 203-204° C. 6.47 —N(n-C₃H₇)₂

—NH₂ 6.48 —N(n-C₃H₇)₂

—NH₂ Melting point 184-185° C. 6.49

C₆F₅O— —NH₂ Melting point 134-135° C. 6.50 —N(CH₃)₂

—NH₂ 6.51 —N(CH₃)₂

—N(CH₃)₂ 6.52 —N(C₂H₅)₂

—NH₂ 6.53

C₆F₅O— —NH₂ Melting point 104-105° C. 6.54 —NHCH₂CH₂CH₃

—NHCH₂CH₂CH₃ Melting point 104-106° C. 6.55

C₆F₅O— —NH₂ Melting point 184-185° C. 6.56

C₆F₅O— —NH₂ Melting point 163-164° C. 6.57

—NH₂ Melting point 193-194° C. 6.58

—NH₂ 6.59 —N(C₂H₅)₂

—NH₂ 6.60

—NH₂ ¹³C-NMR: 166.0 ppm; 164.6 ppm, 159.7 + 156.5 ppm, 153.0 + 149.7 ppm, 105-117 ppm 6.61

C₆F₅O— —NH₂ 6.62 —N(CH₃)₂

—N(CH₃)₂ 6.63

C₆F₅O— —NH₂ Melting point 181-182° C. (Decom- position) 6.64 —N(CH₃)₂

—N(C₂H₅)₂ 6.65 —NHCH₃

—NHCH₃ 6.66 —N(C₂H₅)₂

—N(C₂H₅)₂ 6.67

—NH₂ Melting point 208-209° C. 6.68

—NH₂ 6.69

—NH₂ 6.70 —N(CH₃)₂

—NHCH(CH₃)₂ 6.71 —N(CH₃)₂

—NH₂ 6.72 —NH(CH₂)₃CF₃

—NH₂ Melting point 80-81° C. 6.73

C₆F₅O— —NH₂ Melting point 175-176° C. 6.74

—NH₂ Melting point 147-148° C. 6.75

C₆F₅O— —NH₂ MS: [M⁺+ H, 35%] 492, [M⁺, 40%] 491 6.76

—NH₂ 6.77

C₆F₅O— —NH₂ Melting point 198-199° C. (Decom- position) 6.78 —N(CH₃)₂

—NHC₃H₇ (n) 6.79

—NH₂ 6.80 —N(CH₃)₂

—NHC₂H₅ 6.81

—NH₂ Melting point >220° C. 6.82

—NH₂ 6.83

—NH₂ Melting point 133-134° C. 6.84

C₆F₅O— —NH₂ ¹³C-NMR: 165.4 ppm; 164.5 ppm; 53.7 ppm; 53.4 ppm; 33.3 ppm; 27.3 ppm; 25.9 ppm; 25.4 ppm; 25.3 ppm; 24.3 ppm; 24.2 ppm 6.85

—NH₂ Melting point 144-145°°C. 6.86

C₆F₅O— —NHhd 2 6.87

—NH₂ 6.88 —N(CH₃)₂

—NHCH₃ 6.89

—NH₂ Melting point 187-188° C. 6.90

C₆F₅O— —NH₂ Melting point 187-188° C. (Decom- position) 6.91

—N(CH₃)₂ 6.92

C₆F₅O— —NH₂ ¹³C-NMR: 164.9 ppm; 165.2 ppm; 21.1-53.7 ppm 6.93

C₆F₅O— —NH₂ ¹³C-NMR: 165.7 ppm; 164.7 ppm; 21.2-53.6 ppm 6.94

C₆F₅O— —NH₂ 6.95

—NH₂ 6.96 —N(CH₃)₂

—NH₂ 6.97 —N(C₄H₉(n))₂

—NH₂ 6.98

C₆F₅O— —NH₂ 6.99

C₆F₅S— —NH₂ Melting point 191° C. (Decom- position) 6.100

—NH₂ 6.101

C₆F₅O— —NH₂ 6.102

C₆F₅O— —NH₂ MS: [M⁺+ H] 464 6.103

—NH₂ 6.104

—NH₂ 6.105

—NH₂ Melting point 165-166° C. 6.106

C₆F₅O— —NH₂ 6.107

—NH₂ Melting point 191-192° C. 6.108 —N(C₂H₅)₂

—NH₂ 6.109 —N(CH₃)₂

—NH₂ Melting point 166-167° C. 6.110 —N(CH₃)₂

—NH₂ 6.111

—NH₂ 6.112 —N(CH₃)₂

—NH₂ 6.113

C₆F₅O— —NH₂ Melting point 174-175° C. 6.114

C₆F₅O— —NH₂ 6.115

C₆F₅O— —NH₂ MS: [M⁺+ H] 489 6.116

—NH₂ Melting point 171-172° C. 6.117

C₆F₅O— —NH₂ 6.118

C₆F₅O— —NH₂ 6.119

—NH₂ ¹³C-NMR: 162.9 ppm; 161.8 ppm; 62.5 ppm; 42.8 ppm; 28.8 ppm 28.3 ppm; 27.9 ppm; 27.2 ppm 6.120

—NH₂ Melting point 173-174° C.; ¹³C-NMR: 165.8 ppm; 164.6 ppm, 58.6 ppm; 37.6 ppm; 27.8 ppm; 27.6 ppm; 25.9 ppm; 22.1 ppm, 21.1 ppm 6.121

—NH₂ Melting point 174-175° C. 6.122

C₆F₅O— —NH₂ 6.123

C₆F₅O— —NH₂ 6.124

C₆F₅O— —NH₂ Melting point 161-162° C. 6.125 —N(CH₃)₂

—N(CH₃)₂ 6.126 —N(CH₃)₂

—NH₂ 6.127

—NH₂ ¹H-NMR: 6.8- 7.1 ppm (3H); 5.2 ppm (2H); 3.2-3.5 ppm (6H); 2.6-3.1 ppm (3H); 1.5-1.9 ppm (4H); 1.1-1.3 ppm (6H) 6.128

C₆F₅O— —NH₂ 6.129

—NH₂ Melting point 201-202° C. (Decom- position) 6.130

C₆F₅O— —NH₂ 6.131

C₆F₅O— —NH₂ 6.132

—NH₂ 6.133 —N(CH₃)₂

—NH₂ 6.134

C₆F₅O— —NH₂ 6.135

—NH₂ Melting point 195-196° C. 6.136

C₆F₅O— —NH₂ 6.137

—NH₂ Melting point 151-152° C. 6.138

C₆F₅O— —NH₂ 6.139

—NH₂ Melting point 109-110° C. 6.140

C₆F₅O— —NH₂ Melting point 140-141° C. 6.141

—NH₂ 6.142 —N(CH₃)₂

—NHCH₃ 6.143

—NH₂ Melting point 146-147° C. 6.144

C₆F₅O— —NH₂ 6.145

—NH— Melting point 135-136° C. 6.146 —N(CH₃)₂

—N(CH₃)₂ 6.147

—NH₂ 6.148

—NH₂ 6.149

—NH₂ Melting point 167-168° C. 6.150

—NH₂ 6.151

—NH₂ 6.152

C₆F₅O— —NH₂ 6.153

C₆F₅O— —NH₂ Melting point 161-162° C. 6.154

C₆F₅O— —NH₂ Melting point 166-167° C. 6.155 —N(C₄H₉(n))₂

—N(CH₃)₂ 6.156

—NH₂ 6.157

—NH₂ 6.158

C₆F₅O— —NH₂ 6.159

—NH₂ Melting point 195-196° C. 6.160 —N(CH₃)₂

—N(CH₃)₂ 6.161

—NH₂ 6.162 —N(CH₃)₂

—NHC₄H₉(n) 6.163 —N(CH₃)₂

—NHCH₃ 6.164

—NH₂ Melting point 196-197° C. (Decom- position) 6.165

C₆F₅O— —NH₂ Resin; 2 diastereomers: ¹³C-NMR: 164.3-164.8 ppm (4 signals) 6.166

—NH₂ 6.167

—NH₂ 6.168

C₆F₅O— —NH₂ Melting point 128-129° C. 6.169

C₆F₅O— —NH₂ 6.170

C₆F₅O— —NH₂ Melting point 145-146° C. 6.171 —N(CH₃)₂

—N(CH₃)₂ 6.172 —N(C₂H₅)₂

—NH₂ 6.173

—NH₂ Melting point 139-140° C. 6.174

—NH₂ Melting point 192-193° C. 6.175 —N(CH₃)₂

—N(C₂H₅)₂ 6.176 —N(CH₃)₂

—NH₂ 6.177

C₆F₅O— —NH₂ Melting point 124-125° C. 6.178

—NH₂ 6.179 —N(CH₃)₂

—NH₂ 6.180

—NH₂ 6.181

C₆F₅O— —NH₂ Melting point 180-181° C. 6.182 —N(CH₃)₂

—NH₂ 6.183 —NHC₃H₇(n)

—NH₂ 6.184 —N(CH₃)₂

—NH₂ 6.185

C₆F₅O— —NH₂ Melting point 173-174° C. 6.186 —N(C₂H₅)₂

—NH₂ 6.187

—NH₂ 6.188 —N(CH₃)₂

—N(CH₃)₂ 6.189 —N(C₂H₅)₂

—NH₂ 6.190

—NH₂ 6.191 —N(CH₃)₂

—NH₂ 6.192

C₆F₅O— —NH₂ Melting point 171-172° C. 6.193

—NH₂ 6.194

C₆F₅O— —NH₂ Melting point 168-169° C. 6.195 —N(Ch₃)₂

—NH₂ 6.196 —N(CH₃)₂

—NH₂ 6.197

—NH₂ 6.198

C₆F₅O— —NH₂ 6.199 —N(C₄H₉(n))₂

—N(CH₃)₂ 6.200

C₆F₅O— —NH₂ Melting point 160-161° C. (Decom- position) 6.201

—NH₂ 6.202 —N(CH₃)₂

—N(C₂H₅)₂ 6.203 —NH—C₄H₉(n)

—NH₂ 6.204 —N(CH₃)₂

—NH₂ 6.205

—NH₂ Melting point 160-161° C. 6.206 —N(CH₃)₂

—NH₂ 6.207 —N(CH₃)₂

—NH₂ 6.208 —N(C₂H₅)₂

—NH₂ 6.209

—NH₂ 6.210

C₆F₅O— —NH₂ 6.211

—NH₂ 6.212 —N(C₂H₅)₂

—N(C₂H₅)₂ 6.213 —N(C₂H₅)₂

—NHCH₃ 6.214 —N(CH₃)₂

—NH₂ 6.215

C₆F₅O— —NH₂ Melting point 88-89° C. 6.216

—NH₂ Melting point 179-180° C. 6.217

—NH₂ 6.218 —N(C₂H₅)₂

—N(CH₃)₂ 6.219 —N(CH₃)₂

—NHC₃H₇(n) 6.220 —NHCH₃

—NHCH₃ 6.221

—NH₂ Melting point 169-170° C. (Decom- position) 6.222

C₆F₅O— —NH₂ 6.223

—NH₂ Melting point 168-169° C. 6.224 (CH₃)₂N—

—NH₂ 6.225

—N(C₂H₅)₂ 6.226 —N(C₂H₅)₂

—NHCH₃ 6.227 —N(CH₃)₂

—N(CH₃)₂ 6.228 —N(C₄H₉(n))₂

—NH₂ 6.229

C₆F₅O— —NH₂ Melting point 154-155° C. (Decom- position) 6.230

—NH₂ Melting point 199-200° C. 6.231

—NH₂ Melting point 181-182° C. 6.232

—NH₂ 6.233

C₆F₅O— —NH₂ 6.234

—NH₂ Melting point 160-161° C. 6.235

—NH₂ 6.236 (CH₃)₂N—

—NH₂ 6.237

—NH₂ Melting point 176-177° C. 6.238

—N(CH₃)₂ 6.239

—NH₂ Melting point 188-189° C. 6.240 —N(CH₃)₂

—N(C₂H₅)₂ 6.241 —N(CH₃)₂

—NH₂ 6.242

—NH₂ Melting point 185-186° C. 6.243 —N(CH₃)₂

—NH₂ 6.244 —N(C₂H₅)₂

—NHCH₃ 6.245

—NH₂ 6.246

C₆F₅O— —NH₂ 6.247 —N[CH(CH₃)₂]₂ C₆F₅O— —NH₂ Melting point 153-154° C. 6.248 —N(CH₃)₂

—NH₂ 6.249

—NH₂ Melting point 175-176° C. 6.250 —N(CH₃)₂

—N(CH₃)₂ 6.251 —N(C₂H₅)₂

—NH₂ 6.252

—NHCH₃ 6.253

C₆F₅O— —NH₂ 6.254

—NH₂ Melting point 106-107° C. 6.255 —N(CH₃)₂

—NH₂ 6.256

—NH₂ 6.257

C₆F₅O— —NH₂ Melting point 160-161° C. 6.258 —N(C₂H₅)₂

—NHCH₃ 6.259 —N(CH₃)₂

—N(CH₃)₂ 6.260

—NH₂ ¹H-NMR: 6.8- 7.1 ppm (3H); 5.4 ppm (2H); 3.0-3.4 ppm (2H); 2.7 ppm (1H) 6.261

C₆F₅O— —NH₂ 6.262 —N(CH₃)₂

—NH₂ 6.263 —N(CH₃)₂

—NH₂ 6.264

—NH₂ 6.265

—NH₂ Melting point 172-173° C. (Decom- position) 6.266 —N(CH₃)₂

—NH₂ 6.267 —N(CH₃)₂

—N(C₃H₇(n))₂ 6.268 —N(CH₃)₂

—NH₂ 6.269

C₆F₅O— —NH₂ Melting point 145-146° C. (Decom- position) 6.270

—NH₂ 6.271

—N(CH₃)₂ 6.272 —N(CH₃)₂

—NHC₄H₉(n) 6.273 —N(CH₃)₂

—NH₂ 6.274

C₆F₅O— —NH₂ 6.275

—NH₂ Melting point 153-154° C. 6.276

—NH₂ 6.277 —N(CH₃)₂

—NH₂ 6.278

—NH₂ Melting point 101-103° C. 6.279 —N(C₂H₅)₂

—N(C₂H₅)₂ 6.280

—NH₂ 6.281

C₆F₅O— —NH₂ MS: [M⁺, 50%] 561, [M⁺+ H, 30%] 562 6.282

C₆F₅O— —NH₂ Melting point 157-158° C. 6.283

C₆F₅O— —NH₂ Melting point 133-134° C. 6.284

C₆F₅O— —NH₂ 6.285

C₆F₅O— —NH₂ Melting point 137-138° C. 6.286

C₆F₅O— —NH₂ MS: [M⁺, 50%] 449, [M⁺+ H, 40%] 450 6.287

C₆F₅O— —NH₂ Melting point 129-130° C. 6.288

C₆F₅O— —NH₂ MS: [M⁺, 40%] 449, [M⁺+ H, 40%] 450 6.289

C₆F₅O— —NH₂ Melting point 157-158° C. (Decom- position) 6.290

C₆F₅O— —NH₂ Melting point 112-113° C. 6.291

C₆F₅O— —NH₂ Melting point 154-155° C. 6.292

C₆F₅O— —NH₂ Melting point 165-166° C. 6.293

C₆F₅O— —NH₂ ¹³C-NMR (ppm): 165.8; 164.5; 62.2; 47.7; 41.9; 31.9; 30.7; 29.5; 24.9; 24.8; 19.2 6.294

C₆F₅O— —NH₂ Melting point 181-182° C. 6.295

C₆F₅O— —NH₂ Melting point 162-163° C. 6.296

C₆F₅O— —NH₂ Melting point 147-148° C. 6.297

C₆F₅O— —NH₂ Melting point 134-135° C. 6.298

C₆F₅O— —NH₂ Melting point 158-159° C. 6.299

C₆F₅O— —NH₂ Resin 6.300

C₆F₅O— —NH₂ Melting point 165-166° C. 6.301

C₆F₅O— —NH₂ Melting point 177-178° C. (Decom- position) 6.302

—NH₂ Melting point 174-175° C. 6.303

—N(CH₃)₂ Melting point 125-126° C. 6.304

—OH —NH₂ Melting point 207-208-C. 6.305

—OH —NH₂ Melting point 178-180° C. 6.306

—OH —NH₂ Melting point 176-177° C. 6.307

—OH —NH₂ Melting point 170-171° C. 6.308

—OH —NH₂ Melting point 203-204° C. 6.309

—OH —NH₂ Melting point 187-188° C. 6.310

—N(CH₃)₂ Resin; analysis: C₁₉H₂₉N₅S calc. found  [%]  [%] N 17.88 17.86 S 16.38 16.36 6.311

C₆F₅O— —NH₂ 6.312

C₆F₅O— —NH₂ Melting point 150-151° C. 6.313

C₆F₅O— —NH₂ Melting point 191-192° C. 6.314

C₆F₅O— —NH₂ 6.315

C₆F₅O— —NH₂ 6.316

C₆F₅O— —NH₂ 6.317

C₆F₅O− —NH₂ 6.318

C₆F₅O— —NH₂ 6.319

C₆F₅O— —NH₂ 6.320

—NH₂ Melting point 168-169° C. 6.321

—NH₂ Melting point 174-175° C. (Decom- position) 6.322

C₆F₅O— —NH₂ Melting point 171-172° C. 6.323

C₆F₅O— —NH₂ 6.324

C₆F₅O— —NH₂ Melting point 138-139° C. 6.325

C₆F₅O— —NH₂ Melting point 134-135° C. 6.326

C₆F₅O— —NH₂ Melting point 122-123° C. 6.327

C₆F₅O— —NH₂ 6.328

C₆F₅O— —NH₂ 6.329

C₆F₅O— —NH₂ 6.330

C₆F₅O— —NH₂ 6.331

—NH₂ Melting point 179-180° C. 6.332

C₆F₅O— —NH₂ Melting point 166-167° C. 6.333

C₆F₅O— —NH₂ Melting point 173-174° C. 6.334 —NH-Adamant-1-yl C₆F₅O— —NH₂ 6.335 —NH-Adamant-2-yl C₆F₅O— —NH₂

Example H20 Preparation of 3-amino-5-chloro-1-(3-hexyloxy)thiatriazine

13.6 g of a 22% methylmagnesium chloride solution in THF (0.040 mol) are added to a solution of 4.1 g of 3-hexanol (0.040 mol) in 40 ml of absolute tetrahydrofuran (THF) at a temperature of −70° to −60° C., under a nitrogen atmosphere and with vigorous stirring. After thawing to 20° C., the solution is added dropwise to a solution, cooled to −65° C., of 8.2 g of 1,3,5-trichlorothiatriazine (0.040 mol) in 50 ml of absolute THF, while stirring vigorously. After warming to 0° C., the resulting colourless solution is treated with ammonia, while stirring vigorously. After the intermediate (3,5-dichloro-1-(3-hexyloxy)thiatriazine) has reacted further, 1 l of water is added to the reaction mixture. The resulting suspension is filtered with suction and the residue is rinsed with water and dissolved in methylene chloride, and the solution is dried over sodium sulfate. After the solvent has been evaporated off, the residue is stirred with pentane and the desired product is isolated as white crystals of melting point 144° C. by filtration with suction.

The compounds listed in the following Table 7 can be prepared analogously to Example H20.

TABLE 7 Compounds of the formula VIII (VIII)

Comp. No. Process R₇ R₂ Physical data 7.1 —CH₂CH₂Cl —NH₂ 7.2 —CH₂CH₂C₆H₅ —N(CH₃)C₄H₉(n) 7.3 —CH(CH₃)₂ —NH₂ 7.4 —CH₂CH₂Cl —N(CH₃)₂ 7.5

—NH₂ 7.6

—NH₂ 7.7

—NH₂ 7.8 —CH₂CH₂C₆H₅

7.9

—NH₂ 7.10

—NH₂ 7.11 —CH₂CH₂Cl —NHC(CH₃)₃ 7.12

—NH₂ 7.13 —CH₂CH₂Cl

7.14

—NH₂ 7.15

—NH₂ 7.16

—NH₂ 7.17

—NH₂ 7.18

—NH₂ 7.19

—NH₂ 7.20 —CH₂CH₂Cl

7.21

—NH₂ 7.22

—NH₂ 7.23 —CH₂CH═CH₂ —NH₂ 7.24

—NH₂ 7.25

7.26 —(CH₂)₆CH₃ —NH₂ 7.27

—NH₂ 7.28

—NH₂ 7.29

—NH₂ 7.30 —CH₂CH₂NO₂ —NH₂ 7.31 —CH₂C₆F₅ —NH₂ 7.32

—NH₂ 7.33

—NH₂ 7.34 —CH₃ —NHCH₂CH₂CH₃ 7.35

—NH₂ 7.36

—NH₂ 7.37 —CH₂CH₂Cl

7.38

—NH₂ 7.39 —CH₃ —N(CH₃)₂ 7.40

—NH₂ 7.41

—NH₂ 7.42

—NH₂ 7.43

—NH₂ 7.44

—NH₂ 7.45 —CH₂CH₂Cl —NHCH₂CH₂CH₃ 7.46

—NH₂ 7.47

—NH₂ 7.48

—NH₂ 7.49

—NH₂ 7.50 —CH₂CH₂COOC₂H₅ —NH₂ 7.51

—NH₂ 7.52 —CH₂C≡CH —NH₂ 7.53

—NH₂ 7.54

—NH₂ 7.55 —CH₃ —NH₂ 7.56

—NH₂ 7.57

—NH₂ 7.58

—NHCH₃ 7.59

—NH₂ 7.60

—NH₂ 7.61 —CH₂CH₂CCl₃ —NH₂ 7.62

—NH₂ 7.63

—NH₂ 7.64

—NH₂ 7.65

—NH₂ 7.66

—NH₂ 7.67 —CH₂-adamantyl —NH₂ 7.68

—NH₂ 7.69

—NH₂ 7.70

—NH₂ 7.71

—NH₂ 7.72

—NH₂ 7.73

—NH₂ 7.74

7.75

—NH₂ 7.76 —CH₂CH₂OCH₃ —NH₂ 7.77

—NHC₄H₉(n) 7.78

—NH₂ 7.79

—NH₂ 7.80

—NH₂ 7.81

—NH₂ 7.82 —CH₂CH₂F —NH₂ 7.83

—NH₂ 7.84 —(CH₂)₇CH₃ —NHCH₃ 7.85

—NH₂ 7.86 —C₂H₅ —NH₂ 7.87 —CH(CH₃)C₂H₅ —NH₂ 7.88 —C(CH₃)₃ —NH₂ 7.89

—NH₂ 7.90

—NH₂ 7.91 —CH₃ —NHC(CH₃)₃ 7.92

—NH₂ 7.93

—NH₂ 7.94

—NH₂ 7.95

—NH₂ 7.96

—NH₂ 7.97

—NHCH(CH₃)CH₂OCH₃ 7.98

—NH₂ 7.99

—NH₂ 7.100

—NH₂ 7.101 —C₂H₅ —NH₂ 7.102

—NH₂ 7.103

—NH₂ 7.104

—NH₂ 7.105

—NH₂ 7.106

—NH₂ 7.107

—NH₂ 7.108

—NH₂ 7.109

—NHCH₃ 7.110

—NH₂ 7.111

—NH₂ 7.112

—NH₂ 7.113

—NH₂ 7.114

—NH₂ 7.115

—NH₂ 7.116

—NH₂ 7.117

—NH₂ 7.118

—NH₂ 7.119

—NHC₂H₅ 7.120

—NH₂ 7.121

—NH₂ 7.122

—NH₂ 7.123 —(CH₂)₄CH₃ —NH₂ 7.124

—NH₂ 7.125 —CH₂CH₂SC₂H₅ —NH₂ 7.126 —CH₂CH₂Si(CH₃)₃ —NH₂ 7.127 —(CH₂)₉CH₃ —NH₂ 7.128

—NH₂ 7.129

—NH₂ 7.130

—NH₂ 7.131

—NH₂ 7.132 —(CH₂)₂(CF₂)₃CF₃ —NH₂ 7.133

—NH₂ 7.134 —CH₂CH(C₆H₅)₂ —NH₂ 7.135

—NH₂ 7.136

—NH₂ 7.137

—NH₂ 7.138 —CH₂CH₂Cl —NHCH₂CH₂CH₃ 7.139

—NHC₄H₉(n) 7.140

—NH₂ 7.141

—NH₂ 7.142 —CH₂CH₂Cl —NHCH(CH₃)₂ 7.143 —CH₂CH₂Cl —N(C₂H₅)₂ 7.144

—NH₂ 7.145

—NH₂ 7.146

—NH₂ 7.147 —CH₂CH₂Cl

7.148

—NH₂ 7.149

—NH₂ 7.150

—NH₂ 7.151

—NH₂ 7.152

—NH₂ 7.153

—NH₂ 7.154

—NH₂ 7.155

—NH₂ 7.156

—NH₂ 7.157

—NH₂ 7.158

—NH₂ 7.159

—NH₂ 7.160

—NH₂ 7.161

—NH₂ 7.162

—NH₂ 7.163

—NH₂ 7.164

—NH₂ 7.165

—NH₂ 7.166

—NH₂ 7.167

—NH₂ 7.168

—NH₂ 7.169

—NH₂ 7.170

—NH₂ 7.171

—NH₂ 7.172

—NH₂ 7.173

—NH₂ 7.174

—NH₂ 7.175

—NH₂ 7.176

—NH₂ 7.177

—NH₂ 7.178

—NH₂ 7.179

—NH₂ 7.180

—NH₂ 7.181

—NH₂ 7.182

—NH₂ 7.183

—NH₂ 7.184

—NH₂ 7.185

—NH₂ 7.186

—NH₂ 7.187

—NH₂ 7.188 —(CH₂)₃Si(CH₃)₃ —NH₂ 7.189

—NH₂ 7.190 b₄

—NH₂ Melting point 144° C. (Decomposition) 7.191

—NH₂ 7.192

—NH₂ 7.193 —CH₂Si(CH₃)₃ —NH₂ 7.194

—NHC₂H₅ 7.195

—NHCH₃ 7.196

—NH₂ 7.197

—NH₂ 7.198

—NH₂ 7.199

—NH₂ 7.200

—NH₂ 7.201 —CH(CH₃)—Si(CH₃)₃ —NH₂ 7.202 —CH(CH₃)COOCH₃ —NH₂ 7.203 b₄

—NH₂ Melting point 144° C. 7.204

—NH₂ 7.205 b₄ —CH[CH₂CH(CH₃)₂]₂ —NH₂ ¹H-NMR (CDCl₃, ppm): 6.3 (broad s, 1H); 5,4 (broad s, 1H); 4.25-4.35 (m, 1H); 1.9-1.3(m, 6H); 1.0-0.83(m, 12H) 7.206

—NH₂ 7.207

—NH₂ 7.208

—NH₂ 7.209

—NH₂ 7.210

—NH₂ 7.211

—NH₂ 7.212

—NH₂ 7.213

—NH₂ 7.214

—NH₂ 7.215

—NH₂ 7.216

—NH₂ 7.217

—NH₂ 7.218

—NH₂ 7.219

—NH₂ 7.220

—NH₂ 7.221

—NH₂ 7.222

—NH₂ 7.223

—NH₂ 7.224

—NH₂ 7.225

—NH₂ 7.226

—NH₂ 7.227

—NH₂ 7.228

—NH₂ 7.229

—NH₂ 7.230

—NH₂ 7.231 —CH₂CH₂C₆F₅ —NH₂ 7.232

—NH₂ 7.233

—NH₂ 7.234

—NH₂ 7.235

—NH₂

Example H21 Preparation of 3,5-dichloro-1-(octahydroindol-1-yl)thiatriazine

A mixture of 3.1 g of octahydroindol (0.025 mol) and 2.5 g of triethylamine (0.025 mol) is added dropwise to a solution of 5.1 g of 1,3,5-trichlorothiatriazine (0.025 mol) in 65 ml of diethyl ether at a temperature of −70° to −60° C., under a nitrogen atmosphere and with vigorous stirring. After the reaction mixture has thawed, water is added and the organic phase is washed with water, sodium bicarbonate solution and brine, dried over sodium sulfate and evaporated. After crystallization from pentane, crystals of the desired compound of melting point 90-92° C. are isolated.

The compounds listed in the following Table 8 can be prepared analogously to Example H21.

TABLE 8 Compounds of the the formula IX (IX)

Comp. No. R₁ Physical data 8.1 —NHCH₂CH₂CH₃ 8.2

8.3

8.4

8.5

8.6

8.7

8.8

8.9

8.10

8.11

8.12

8.13

8.14

8.15 —N(CH₂CH₂CN)₂ 8.16 —NHC₆H₁₁(c) 8.17 —N(n-C₃H₇)₂ 8.18

8.19

8.20

8.21

8.22

8.23

8.24

8.25

8.26

8.27

8.28

8.29

8.30

8.31 —N[CH(CH₃)₂]₂ 8.32 —(C₂H₅)₂ 8.33 —N(C₂H₅)C₄H₉(n) 8.34

8.35

8.36

8.37 —N(CH₃)₂ 8.38

8.39

8.40

8.41

8.42 —N(C₂H₅)₂ 8.43

(not isolated) 8.44

8.45

8.46

8.47

8.48

8.49

8.50 —NHCH₃ 8.51

8.52

8.53 —NH(CH₂)₃CF₃ 8.54

8.55

8.56

8.57

8.58

8.59

8.60

8.61

8.62

8.63

8.64

8.65

8.66

8.67

8.68

8.69 —N(C₄H₉(n))₂ 8.70

8.71

8.72

8.73

8.74

8.75

8.76

8.77

8.78

8.79

8.80

Melting point 90-92° C. 8.81

8.82

8.83 —N(CH₃)₂ 8.84

8.85

8.86

8.87

8.88

8.89

8.90

8.91

8.92

8.93

8.94

8.95

8.96

8.97

8.98

8.99

8.100

8.101

8.102

8.103 —N(C₄H₉(n))₂ 8.104

8.105

8.106

8.107

8.108

8.109

8.110

8.111

8.112

8.113

8.114

8.115 —NHC₃H₇(n) 8.116

8.117

8.118

8.119

8.120

8.121

8.122

8.123 —NH—C₄H₉(n) 8.124

8.125

8.126

8.127

8.128

8.129

8.130

8.131

8.132

8.133

8.134

8.135

8.136

8.137

8.138

8.139 —N[CH(CH₃)₂]₂ 8.140

8.141

8.141

8.143

8.144

8.145

8.146

8.147

8.148

8.149

8.150

8.151

8.152

8.153

8.154

8.155

8.156

8.157

8.158

(not isolated) 8.159

8.160

8.161

8.162

8.163

8.164

8.165

8.166

8.167

8.168

8.169

8.170

8.171

8.172

8.173

8.174

8.175

8.176

8.177

8.178

8.179

8.180

8.181

8.182

8.183

8.184

8.185

8.186

8.187

8.188

Example H22 Preparation of 3-amino-5-chloro-1-(piperidin-1-yl)thiatriazine

15.6 ml of a 1.6 molar n-butyllithium solution in hexane (0.025 mol) are added to a solution of 2.13 g of piperidine (0.025 mol) in 10 ml of absolute tetrahydrofuran at a temperature of −70° to −60° C., under a nitrogen atmosphere and with vigorous stirring. After thawing to 20° C., the resulting white suspension is added dropwise in portions to a solution, cooled to −60° C., of 5.11 g of 1,3,5-trichlorothiatriazine (0.025 mol) in 50 ml of absolute tetrahydrofuran, while stirring vigorously. After warming to −10° C. the reaction mixture is treated with ammonia (gas) with vigorous stirring. After all the intermediate has been used up, water and ethyl acetate are added to the reaction mixture. The organic phase is washed with water and brine, dried over sodium sulfate and evaporated. The residue is stirred with a diethyl ether/pentane mixture and filtered off with suction. The desired compound is isolated as yellowish crystals of melting point 118-120° C. (decomposition).

Example H23 Preparation of 3-amino-5-chloro-1-(octahydroindol-1-yl)thiatriazine

10.2 g of a 30% ammonia solution in water (0.180 mol) are added to a solution of 3.7 g of 3,5dichloro-1-(octahydroindol-1-yl)thiatriazine (0.0126 mol) in 120 ml of tetrahydrofuran at 20° C. and the mixture is stirred vigorously for 3 hours. After evaporation of the organic solvent, the resulting suspension is filtered off with suction and the residue is washed with water and then with diethyl ether and dried. The desired compound is isolated as slightly yellowish crystals of melting point 115° C. (decomposition).

The compounds listed in the following Table 9 can be prepared analogously to Examples H22 and H23.

TABLE 9 Compounds of the formula X (X)

Comp. No. R₁ R₂ Physical data 9.1 —NHCH₂CH₂CH₃ —NH₂ 9.2

—N(CH₃)₂ 9.3

—NH₂ 9.4

—NH₂ 9.5

—NH₂ 9.6

—NH₂ 9.7

—NH₂ 9.8

—NH₂ 9.9

—NH₂ 9.10

—NH₂ 9.11

—NH₂ 9.12

—NH₂ 9.13

—NH₂ 9.14

—NH₂ 9.15

—NH₂ 9.16 —N(CH₂CH₂CN)₂ —NH₂ 9.17 —NHC₆H₁₁(c) —NH₂ 9.18

—NH₂ 9.19 —N(n-C₃H₇)₂ —NH₂ 9.20

—NH₂ 9.21

—NH₂ 9.22

—NH₂ 9.23

—NH₂ 9.24

—NH₂ 9.25

—NH₂ 9.26

—NH₂ 9.27

—NH₂ 9.28

—NH₂ 9.29

—NH₂ 9.30

—NH₂ 9.31

—NH₂ 9.32

—NH₂ 9.33 —N[CH(CH₃)₂]₂ —NH₂ 9.34 —N(C₂H₅)C₄H₉(n) —NHCH₃ 9.35

—NH₂ 9.36

—NH₂ 9.37

—NH₂ 9.38

—NHCH(CH₃)₃ 9.39

—NH₂ 9.40

—NH₂ 9.41 —N(n-C₃H₇)₂ —NH₂ 9.42

—NH₂ 9.43 —N(CH₃)₂ —NH₂ 9.44 —N(CH₃)₂ —N(CH₃)₂ 9.45 —N(C₂H₅)₂ —NH₂ 9.46

—NH₂ Melting point 118-120° C. (Decomposition) 9.47 —NHCH₂CH₂CH₃ —NHCH₂CH₂CH₃ 9.48

—NH₂ 9.49

—NH₂ 9.50

—NH₂ 9.51

—NH₂ 9.52

—NH₂ 9.53

—NH₂ 9.54

—NH₂ 9.55 —N(CH₃)₂ —N(C₂H₅)₂ 9.56 —NHCH₃ —NHCH₃ 9.57 —N(C₂H₅)₂ —N(C₂H₅)₂ 9.58

—NH₂ 9.59

—NH₂ 9.60 —N(CH₃)₂ —NHCH(CH₃)₂ 9.61 —NH(CH₂)₃CF₃ —NH₂ 9.62

—NH₂ 9.63

—NH₂ 9.64

—NH₂ 9.65

—NH₂ 9.66

—NH₂ 9.67 —N(CH₃)₂ —NHC₃H₇(n) 9.68

—NH₂ 9.69 —N(CH₃)₂ —NHC₂H₅ 9.70

—NH₂ 9.71

—NH₂ 9.72

—NH₂ 9.73

—NH₂ 9.74

—NH₂ 9.75 —N(CH₃)₂ —NHCH₃ 9.76

—N(CH₃)₂ 9.77

—NH₂ 9.78

—NH₂ 9.79

—NH₂ 9.80

—NH₂ 9.81 —N(C₄H₉(n))₂ —NH₂ 9.82

—NH₂ 9.83

—NH₂ 9.84

—NH₂ 9.85

—NH₂ 9.86

—NH₂ 9.87

—NH₂ 9.88

—NH₂ 9.89

—NH₂ 9.90

—NH₂ 9.91

—NH₂ 9.92

—NH₂ 9.93

—NH₂ Melting point 115° C. (Decomposition) 9.94

—NHCH₃ 9.95

—NH₂ 9.96

—NH₂ 9.97

—NH₂ 9.98

—NH₂ 9.99

—NH₂ 9.100

—NH₂ 9.101

—NH₂ 9.102

—NH₂ 9.103

—NH₂ 9.104

—NH₂ 9.105

—NH₂ 9.106

—NH₂ 9.107

—NH₂ 9.108

—NH₂ 9.109

—NH₂ 9.110

—NH₂ 9.111

—NH₂ 9.112

—NH₂ 9.113

—NH₂ 9.114

—NH₂ 9.115

—NH₂ 9.116

—NH₂ 9.117 —N(C₄H₉(n))₂ —N(CH₃)₂ 9.118

—NH₂ 9.119

—NH₂ 9.120

—NH₂ 9.121

—NH₂ 9.122 —N(CH₃)₂ —NHC₄H₉(n) 9.123

—NH₂ 9.124

—NH₂ 9.125

—NH₂ 9.126

—NH₂ 9.127

—NH₂ 9.128

—NH₂ 9.129

—NH₂ 9.130 —NHC₃H₇(n) —NH₂ 9.131

—NH₂ 9.132

—NH₂ 9.133

—NH₂ 9.134

—NH₂ 9.135

—NH₂ 9.136

—NH₂ 9.137

—NH₂ 9.138 —NH—C₄H₉(n) —NH₂ 9.139

—NH₂ 9.140 —N(C₂H₅)₂ —NHCH₃ 9.141

—NH₂ 9.142

—NH₂ 9.143 —N(C₂H₅)₂ —N(CH₃)₂ 9.144

—NH₂ 9.145

—NH₂ 9.146

—NH₂ 9.147

—N(C₂H₅)₂ 9.148

—NH₂ 9.149

—NH₂ 9.150

—NH₂ 9.151

—NH₂ 9.152

—N(CH₃)₂ 9.153

—NH₂ 9.154

—NH₂ 9.155

—NH₂ 9.156 —N[CH(CH₃)₂]₂ —NH₂ 9.157

—NH₂ 9.158

—NHCH₃ 9.159

—NH₂ 9.160

—NH₂ 9.161

—NH₂ 9.162

—NH₂ 9.163 —N(CH₃)₂ —N(C₃H₇(n))₂ 9.164

—NH₂ 9.165

—N(CH₃)₂ 9.166 —N(CH₃)₂ —NHC₄H₉(n) 9.167

—NH₂ 9.168

—NH₂ 9.169

—NH₂ 9.170

—NH₂ 9.171

—NH₂ 9.172

—NH₂ 9.173

—NH₂ 9.174

—NH₂ 9.175

—NH₂ 9.176

—NH₂ 9.177

—NH₂ 9.178

—NH₂ 9.179

—NH₂ 9.180

—NH₂ 9.181

—NH₂ 9.182

—NH₂ 9.183

—NH₂ 9.184

—NH₂ 9.185

—NH₂ 9.186

—NH₂ 9.187

—NH₂ 9.188

—NH₂ 9.189

—NH₂ 9.190

—NH₂ 9.191

—NH₂ 9.192

—NH₂ 9.193

—N(CH₃)₂ 9.194

—NH₂ 9.195

—NH₂ 9.196

—NH₂ 9.197

—NH₂ 9.198

—NH₂ 9.199

—NH₂ 9.200

—NH₂ 9.201

—NH₂ 9.202

—NH₂ 9.203

—NH₂ 9.204

—NH₂ 9.205

—NH₂ 9.206

—NH₂ 9.207

—NH₂ 9.208

—NH₂ 9.209

—NH₂ 9.210

—NH₂ 9.211

—NH₂ 9.212

—NH₂ 9.213

—NH₂ 9.214

—NH₂ 9.215

—NH₂ 9.216

—NH₂ 9.217

—NH₂

Formulation examples for active compounds of the formula I

(%=percent by weight)

F1. Emulsion concentrates a) b) c) d) Active compound according  5% 10% 25% 50% to Tables 4-6 Calcium dodecylbenzenesulfonate  6%  8%  6%  8% Castor oil polyglycol ether  4% —  4%  4% (36 mol of EO) Octylphenol polyglycol ether —  4% —  2% (7-8 mol of EO) Cyclohexanone — — 10% 20% Aromatic hydrocarbon mixture 85% 78% 55% 16% C₉-C₁₂

Emulsions of any desired concentration can be prepared from such concentrates by dilution with water.

F2. Solutions a) b) c) d) Active compound according  5% 10% 50% 90% to Tables 4-6 1-Methoxy-3-(3-methoxypropoxy)propane — 20% 20% — Polyethylene glycol molecular weight 400 20% 10% — — N-Methyl-2-pyrrolidone — — 30% 10% Aromatic hydrocarbon mixture 75% 60% — — C₉-C₁₂

The solutions are suitable for use in the form of tiny drops.

F3. Wettable powders a) b) c) d) Active compound according  5% 25% 50% 80% to Tables 4-6 Sodium lignin sulfonate  4% —  3% — Sodium lauryl sulfate  2%  3% —  4% Sodium diisobutyl-naphthaline sulfonate —  6%  5% 6% Octylphenol polyglycol ether —  1%  2% — (7-8 Mol EO) Highly disperse silicic acid 1%  3%  5% 10% Kaolin 88% 62% 35% —

The active compound is mixed thoroughly with the additives and the mixture is ground thoroughly in a suitable mill. Wettable powders which can be diluted with water to give suspensions of any desired concentration are obtained.

F4. Coated granules a) b) c) Active compound according  0.1%  5% 15% to Tables 4-6 Highly disperse silicic acid  0.9%  2%  2% Inorganic carrier (ø0.1-1 mm), for example 99.0% 93% 83% CaCO₃ or SiO₂

The active compound is dissolved in methylene chloride, the solution is sprayed onto the carrier and the solvent is then evaporated off in vacuo.

F5. Coated granules a) b) c) Active compound according  0.1%  5% 15% to Tables 4-6 Polyethylene glycol molecular weight 200  1.0%  2%  3% Highly disperse silicic acid  0.9%  1%  2% Inorganic carrier (ø0.1-1 mm), for example 98.0% 92% 80% CaCO₃ or SiO₂

The finely ground active compound is applied uniformly to the carrier, which has been moistened with polyethylene glycol, in a mixer. Dust-free coated granules are obtained in this manner.

F6. Extruded granules a) b) c) d) Active compound according 0.1% 3% 5% 15% to Tables 4-6 Sodium lignin sulfonate 1.5% 2% 3%  4% Carboxymethyl cellulose 1.4% 2% 2%  2% Kaolin 97.0%  93%  90%  79%

The active compound is mixed with the additives and the mixture is ground and moistened with water. This mixture is extruded and the extrudate is then dried in a stream of air.

F7. Dusts a) b) c) Active compound according  0.1%  1%  5% to Tables 4-6 Talc 39.9% 49% 35% Kaolin 60.0% 50% 60%

Ready-to-use dusts are obtained by mixing the active compound with the carriers and grinding the mixture on a suitable mill.

F8. Suspension concentrates a) b) c) d) Active compound according   3%  10%  25%  50% to Tables 4-6 Ethylene glycol   5%   5%   5%   5% Nonylphenol polyglycol ether —   1%   2% — (15 mol of EO) Sodium lignin sulfonate   3%   3%   4%   5% Carboxymethyl cellulose   1%   1%   1%   1% 37% aqueous formaldehyde solution 0.2% 0.2% 0.2% 0.2% Silicone oil emulsion 0.8% 0.8% 0.8% 0.8% Water  87%  79%  62%  38%

The finely ground active compound is mixed intimately with the additives. A suspension concentrate from which suspensions of any desired concentration can be prepared by dilution with water is thus obtained.

BIOLOGICAL EXAMPLES Example B1 Herbicidal Action Before Emergence of the Plants (Pre-emergent Action)

Monocotyledon and dicotyledon test plants are sown in standard soil in plastic pots. Immediately after sowing, the test substances are sprayed on (500 l of water/ha) in an aqueous suspension prepared from a 25% wettable powder (Example F3, b)), corresponding to a dosage of 2000 g of active substance/ha. The test plants are then grown under optimum conditions in a greenhouse. After a test period of 3 weeks, the test is evaluated with a ratings scale of nine levels (1=complete damage, 9=no action). Ratings of 1 to 4 (in particular 1 to 3) mean a good to very good herbicidal action.

Test plants: Avena, Setaria, Sinapis, Stellaria

In this test, the compounds of the formula I according to the examples in Tables 4, 5 and 6 show a potent herbicidal action.

Table B1 gives examples of the good herbicidal activity of the compounds of the formula I:

TABLE B1 Pre-emergent action Test plants Compound No. Avena Setaria Sinapis Stellaria 5.52  4 2 1 1 5.78  3 2 2 1 5.86  5 3 1 1 5.120 4 2 1 1 5.127 4 2 1 1 5.131 4 2 1 1 5.146 4 1 1 1 5.176 4 2 1 1 5.317 4 2 2 1 5.321 3 1 1 1 5.326 4 4 1 1 5.327 4 3 2 1 5.329 2 1 1 1 5.332 3 1 1 1 6.10  4 4 1 1 6.27  4 3 2 1 6.30  3 2 1 1 6.34  3 1 1 1 6.37  3 2 1 1 6.42  4 2 1 1 6.53  3 3 1 1 6.63  4 3 1 1 6.77  4 3 1 1 6.89  2 2 1 1 6.92  4 1 1 1 6.93  2 1 1 1 6.124 3 1 1 1 6.129 4 4 1 1 6.135 3 3 1 1 6.140 4 3 2 1 6.145 4 2 1 1 6.153 4 3 1 1 6.154 4 1 1 1 6.170 3 4 4 1 6.173 4 3 1 1 6.185 4 4 1 1 6.192 2 1 1 1 6.194 7 5 2 2 6.200 4 1 1 1 6.229 3 2 1 1 6.257 3 2 1 1 6.282 4 2 1 1 6.285 5 2 1 1 6.292 5 1 1 1 6.295 3 1 1 1 6.296 4 2 1 1 6.298 3 2 1 1 6.302 3 2 1 1 6.331 4 2 1 1

The same results are obtained when the compounds of the formula I are formulated according to Examples F1, F2 and F4 to F8.

Example B2 Post-emergent Herbicidal Action (Contact Herbicide)

Monocotyledon and dicotyledon test plants are grown in plastic pots with standard soil in a greenhouse and, in the 4- to 6-leaf stage, are sprayed with an aqueous suspension of the test substances of the formula 1, prepared from a 25% wettable power (Example F3, b)), corresponding to a dosage of 2000 g of active substance/ha (500 l of water/ha). The test plants are then grown further in the greenhouse under optimum conditions. After a test period of about 18 days, the test is evaluated with a ratings scale of 9 levels (1=complete damage, 9=no action). Ratings of 1 to 4 (in particular 1 to 3) mean a good to very good herbicidal action.

Test plants: Sinapis, Stellaria

In this test also, the compounds of the formula I according to the examples in Tables 4, 5 and 6 show a good herbicidal action.

Table B2 gives examples of the good herbicidal activity of the compounds of the formula I:

TABLE B2 Post-emergent action Test plants Compound No. Sinapis Stellaria 5.52  2 2 5.59  1 3 5.78  2 3 5.85  3 3 5.120 2 3 5.127 2 3 5.131 1 3 5.141 2 4 5.154 2 4 5.176 2 2 5.316 2 4 5.317 2 4 5.318 2 4 5.321 2 2 5.326 2 4 5.329 1 5 5.332 1 2 5.337 1 5 6.6  2 4 6.7  2 3 6.17  3 4 6.21  2 4 6.23  2 4 6.27  2 3 6.30  2 3 6.34  2 2 6.37  3 2 6.42  2 2 6.57  2 4 6.81  2 3 6.89  2 3 6.90  2 4 6.92  1 1 6.93  1 1 6.102 2 3 6.120 2 4 6.124 2 3 6.129 2 3 6.135 3 3 6.140 2 3 6.145 3 3 6.153 1 2 6.154 1 1 6.164 1 3 6.168 2 3 6.170 2 3 6.173 2 3 6.177 2 2 6.181 2 3 6.185 1 1 6.192 2 4 6.194 2 4 6.200 2 2 6.229 2 3 6.247 3 4 6.249 1 2 6.257 2 2 6.282 1 5 6.283 1 4 6.285 2 3 6.292 2 3 6.295 1 3 6.296 2 4 6.298 1 4 6.302 2 3 6.331 1 2 6.320 2 3

The same results are obtained when the compounds of the formula I are formulated according to Examples F1, F2 and F4 to F8. 

What is claimed is:
 1. A compound of the formula I

in which R₁ is a group —OR₇, —NR₉₀R₉₁ or

in which the radicals R₂₀ independently of one another are hydrogen, C₁-C₄alkyl or C₁-C₃alkoxy; R₂₅ is hydrogen, chlorine, methyl or methoxy; R₁₀₀ is hydrogen or C₁-C₃alkyl; Y₁ is —O—, —S— or —NR₃₀; R₃₀ is hydrogen, methyl, C₁-C₃alkylcarbonyl or (C₁-C₃alkyl)₂NCO; n₁ is 1, 2, 3, 4 or 5; n₂ is 0, 1 or 2; and n₃ is a number from 3 to 10; R₇ is C₁-C₁6alkyl, C₁-C₁₆alkyl substituted by up to 9 halogens, up to 3 NO₂, CN, C₁-C₅alkoxy, C₁-C₅alkylthio, C₃-C₈cycloalkoxy, C₃-C₈cycloalkylthio, C₁-C₃trialkylsilyl, C₃-C₁₀alkenyloxy, C₃-C₅alkynyloxy, C₁-C₅alkylcarbonyloxy, C₁-C₃alkoxycarbonyl, C₁-C₃alkylcarbonyl, C₅-C₇cycloalkenyl or C₅-C₇cycloalkenyl substituted up to 3 times by C₁-C₄alkyl, or R₇ is C₁-C₁₆alkyl substituted once by C₃-C₈cycloalkyl, C₆-C₁₂bicycloalkyl, C₆-C₁₂chlorobicycloalkyl, C₆-C₁₂bicycloalkenyl or adamantyl, or R₇ is C₁-C₁₆alkyl substituted once by up to 5 times substituted or unsubstituted aryl, aryloxy, arylmethyleneoxy, arylcarbonyl, arylcarbonyloxy or a heterocyclic ring of the formula

in which R₉₈ is hydrogen, fluorine, chlorine, bromine, CN, C₁-C₃alkoxy, C₁-C₃alkoxycarbonyl, C₁-C₃alkoxy-C₁-C₃alkyl, C₁- or C₂halogenoalkyl, C₁-C₅alkyl, NO₂, C₃-C₅alkenyl, cyclopropyl or C₁- or C₂halogenoalkoxy; R₁₀₀ is as defined above; R₂₄ is hydrogen or methyl; and R₁₀₁ is C₁-C₄alkyl, C₁-C₄alkylcarbonyl or C₁-C₃-alkoxycarbonyl, or R₇ is C₃-C₁₅alkenyl, C₃-C₁₅alkenyl substituted by up to 9 halogens, up to 3 C₁-C₃alkoxy, C₃-C₈cycloalkyl, C₁-C₃trialkylsilyl or up to 5 times substituted or unsubstituted aryl or aryloxy, or R₇ is C₃-C₅alkynyl, C₃-C₁₂cycloalkyl, C₃-C₁₂cycloalkyl substituted by up to 9 halogens, up to 3 CN, C₁-C₃trialkylsilyl, ═O, C₁-C₆alkyl, cyano-C₁-C₅alkyl, C₁-C₅alkyl-CONH—C₁-C₅alkyl, phenyl-CONH—C₁-C₅alkyl, C₁-C₅chloroalkyl, C₁-C₃alkoxy, C₁-C₃alkylthio, C₁-C₃alkoxycarbonyl, C₁-C₃alkoxycarbonyl-C₁-C₅alkyl, C₅-C₇cycloalkyl, C₂-C₄alkenyl, C₂-C₄alkynyl, benzyl or C₁-C₃halogenoalkyl, or R₇ is C₅-C₇cycloalkenyl, C₅-C₇cycloalkenyl substituted up to 3 times by C₁-C₃alkyl, or R₇ is C₆-C₁₂bicycloalkyl, C₆-C₁₂bicycloalkyl substituted up to 3 times by C₁-C₃alkyl, cyano or halogen, C₆-C₁₂bicycloalkenyl or C₆-C₁₂bicycloalkenyl substituted up to 3 times by C₁-C₃alkyl, or R₇ is a substituted or unsubstituted non-aromatic heterocyclic ring of the formula

in which R₁₀₀ and R₁₀₁ are as defined above, or an alicyclic ring system; R₉₀ and R₉₁ independently of one another are hydrogen, C₁-C₁₂alkyl, C₁-C₁₂alkyl substituted by up to 3 halogens, NO₂, CN, hydroxyl, C₁-C₃alkoxy, C₁-C₃alkoxycarbonyl, C₁-C₃trialkylsilyl, C₁-C₆alkylamino, di(C₁-C₆alkyl)amino, C₃-C₇cycloalkyl,

 or a heterocyclic ring of the formula

in which R₂₅ and R₁₀₀ are as defined above, or C₃-C₁₀alkenyl, C₃-C₁₀alkynyl, C₆-C₁₂bicycloalkyl, C₆-C₁₂bicycioalkenyl, C₃-C₁₂cycloalkyl, C₃-C₁₂cycloalkyl substituted up to 4 times by C₁-C₄alkyl, C₅-C₇cycloalkenyl or C₅-C₇cycloalkenyl substituted up to 4 times by C₁-C₄alkyl, with the proviso that R₉₀ and R₉₁ are not simultaneously hydrogen; or R₉₀ and R₉₁, together with the nitrogen atom to which they are bonded, form a saturated heterocyclic ring which contains 2-12 carbon atoms and can contain, as further heteroatoms, a nitrogen, an oxygen or a sulfur atom and can be substituted up to 3 times by C₁-C₄alkyl, C₁- or C₂halogenoalkyl, C₁- or C₂hydroxyalkyl, methoxy-C₁-C₄alkyl, halogen, hydroxyl, CN, C₁-C₄alkoxy, C₁-C₄alkylcarbonyl, C₁- or C₂halogenoalkyl,

 C₁-C₃alkoxycarbonyl, (C₁-C₃alkyl)₂NCO, di(C₁-C₄alkyl)amino or ═O and can additionally be bridged by 1 or 2

 groups and onto which 1 or 2 further carbocyclic, heterocyclic or aromatic rings can be fused, or R₉₀ and R₉₁, together with the nitrogen atom to which they are bonded, form a mono- or diunsaturated heterocyclic ring which contains 5-7 carbon atoms and is substituted up to 3 times or unsubstituted by C₁-C₄alkyl, C₁- or C₂halogenoalkyl, halogen, hydroxyl, CN, amino, C₁-C₄alkylamino, di(C₁-C₄alkyl)amino, phenyl, C₁-C₄alkoxy or C₁-C₃alkoxycarbonyl and additionally bridged by 1 or 2

 groups and onto which 1 or 2 further carbocyclic, heterocyclic or aromatic rings can be fused; the radicals R₂₄ independently of one another are hydrogen or methyl; R₉₈ is hydrogen, fluorine, chlorine, bromine, CN, C₁-C₃alkoxy, C₁-C₃alkoxycarbonyl, C₁-C₃alkoxy-C₁-C₃alkyl, C₁- or C₂halogenoalkyl, C₁-C₅alkyl, NO₂, C₃-C₅alkenyl, cyclopropyl or C₁- or C₂halogenoalkoxy; R₂ is halogen, C₁-C₁₀alkoxy, C₁-C₁₀alkoxy substituted up to 3 times by halogens, CN, NO₂, C₁-C₆alkoxy, C₁-C₆alkylthio, C₃-C₆alkenyloxy, C₁-C₆alkoxycarbonyl, heterocyclyl of the formula

in which R₂₄, R₉₈, R₁₀₀ and R₁₀₁ are as defined above, or substituted up to 5 times or unsubstituted aryl or aryloxy, C₃-C₁₀alkenyloxy, C₃-C₁₀alkenyloxy substituted up to 3 times by halogens, CN, NO₂, C₁-C₆alkoxy, C₃-C₆alkenyloxy, C₁-C₆alkoxycarbonyl or substituted up to 5 times or unsubstituted aryl or aryloxy, C₁-C₁₀alkylthio, C₁-C₁₀alkylthio substituted up to 3 times by halogens, CN, NO₂, C₁-C₆alkoxy, C₃-C₆alkenyloxy, C₁-C₆alkoxycarbonyl or substituted up to 5 times or unsubstituted aryl or aryloxy, C₃-C₁₀alkenylthio or C₃-C₁₀alkenylthio substituted up to 3 times by halogens, CN, NO₂, C₁-C₆alkoxy, C₃-C₆alkenyloxy, C₁-C₆alkoxycarbonyl or substituted up to 5 times or unsubstituted aryl or aryloxy, or R₂ is C₃-C₅alkynyloxy, C₃-C₅alkynylthio, C₃-C₈cycloalkyl-X—, C₆-C₁₂bicycloalkyl-X—, heterocylyl-X—, alicyclyl-X—, aryl-X—, phthalidyl-X—, biphenyl-X— or heteroaryl-X—; X is —O—, —S—, —SO— or —SO₂—, or R₂ is a group R₈₈R₈₉N—,

R₈₈ and R₈₉ independently of one another are hydrogen, C₁-C₆alkyl, C₁-C₆alkyl substituted up to 3 times by halogens, CN, C₁-C₃alkoxy or

 C₃-C₁₂cycloalkyl, C₃-C₁₀alkenyl, C₃-C₁₀alkynyl, C₆-C₁₂bicycloalkyl or C₆-C₁₂bicycloalkyl substituted up to 3 times by C₁-C₃alkyl; the radicals R₂₀ independently of one another are hydrogen or C₁-C₄alkyl; n₇ is 4 or 5; Y is —O—, —S—, —NH— or —NR₁₀₁—; R₉₈ and R₁₀₁ are as defined above; R₃ is halogen, hydroxyl, C₁-C₁₀alkoxy, C₁-C₁₀alkoxy substituted up to 3 times by halogens, CN, NO₂, C₁-C₆alkoxy, C₁-C₆alkylthio, C₃-C₆alkenyloxy, C₁-C₆alkoxycarbonyl, heterocyclyl of the formula

in which R₂₄, R₉₈, R₁₀₀ and R₁₀₁ are as defined above, or substituted up to 5 times or unsubstituted aryl or aryloxy, C₃-C₁₀alkenyloxy, C₃-C₁₀alkenyloxy substituted up to 3 times by halogens, CN, NO₂, C₁-C₆alkoxy, C₃-C₆alkenyloxy, C₁-C₆alkoxycarbonyl or substituted up to 5 times or unsubstituted aryl or aryloxy, C₁-C₁₀alkylthio, C₁-C₁₀alkylthio substituted up to 3 times by halogens, CN, NO₂, C₁-C₆alkoxy, C₃-C₆alkenyloxy, C₁-C₆alkoxycarbonyl or substituted up to 5 times or unsubstituted aryl or aryloxy, C₃-C₁₀alkenylthio or C₃-C₁₀alkenylthio substituted up to 3 times by halogens, CN, NO₂, C₁-C₆alkoxy, C₃-C₆alkenyloxy, C₁-C₆alkoxycarbonyl or substituted up to 5 times or unsubstituted aryl or aryloxy, or R₃ is C₃-C₅alkynyloxy, C₃-C₅alkynylthio, C₃-C₈cycloalkyl-X—, C₆-C₁₂bicycloalkyl-X—, heterocyclyl-X—, alicyclyl-X—, aryl-X—, phthalidyl-X—, biphenyl-X— or heteroaryl-X—; and X is as defined above, and stereoisomers of the compounds of the formula I, excluding the compounds of formulae I₁ to I₇:

wherein R₀₁ is hydrogen, methyl, ethyl, n-propyl, i-butyl, tert-butyl, allyl, cyclohexyl or benzyl; R₀₂ is ethyl, benzyl or i-butyl and R₀₃ is ethyl, cyclohexyl, benzyl or i-butyl, or R₀₂ and R₀₃, together with the nitrogen atom to which they are bonded, form a piperidine ring; R₀₄ is chlorine, methylthio, ethylthio, i-propylthio, n-butylthio, i-butylthio, phenylthio or benzylthio; R₀₅ is ethoxy, methylthio, ethylthio or phenylthio; and R₀₆ is chlorine or cyclohexylamino.
 2. A compound according to claim 1, in which R₁ is a group —OR₇, —NR₉₀R₉₁ or

in which the radicals R₂₀ independently of one another are hydrogen, C₁-C₄alkyl or C₁-C₃alkoxy; R₂₅ is hydrogen, chlorine, methyl or methoxy; R₁00 is hydrogen or C₁-C₃alkyl; Y₁ is —O—, —S— or —NR₃₀; R₃₀ is hydrogen, methyl, C₁-C₃alkylcarbonyl or (C₁-C₃alkyl)₂NCO; n₁ is 1, 2, 3,4 or 5; n₂ is 0, 1 or 2; and n₃ is a number from 3 to 10; R₇ is C₁-C₁₆alkyl, C₁-C₁₆alkyl substituted by halogen, NO₂, CN, C₁-C₅alkoxy, C₁-C₅alkylthio, C₃-C₈cycloalkoxy, C₁-C₃trialkylsilyl, C₃-C₁₀alkenyloxy, C₃-C₅alkynyloxy, C₁-C₅alkyl-carbonyloxy, C₁-C₃alkoxycarbonyl, C₁-C₃alkylcarbonyl, C₅-C₇cycloalkenyl or C₅-C₇cycloalkenyl substituted by C₁-C₄alkyl, or R₇ is C₁-C₁₆alkyl substituted by C₃-C₈cycloalkyl, C₆-C₁₂bicycloalkyl, C₆-C₁₂chlorobicycloalkyl, C₆-C₁₂bicycloalkenyl or adamantyl, or R₇ is C₁-C₁₆alkyl substituted by substituted or unsubstituted aryl, aryloxy, arylmethylenoxy, arylcarbonyl, arylcarbonyloxy or a heterocyclic ring of the formula

in which R₂₄, R₉₈, R₁₀₀ and R₁₀₁ are as defined in claim 1, or R₇ is C₃-C₁₅alkenyl, C₃-C₁₅alkenyl substituted by halogen, C₁-C₃alkoxy, C₃-C₈cycloalkyl or substituted or unsubstituted aryl or aryloxy, or R₇ is C₃-C₅alkynyl, C₃-C₁₂cycloalkyl, C₃-C₁₂cycloalkyl substituted by halogen, CN, C₁-C₃-trialkylsilyl, ═O, C₁-C₆alkyl, cyano-C₁-C₅alkyl, C₁-C₅alkyl-CONH—C₁-C₅alkyl, phenyl-CONH—C₁-C₅alkyl, C₁-C₅chloroalkyl, C₁-C₃alkoxy, C₁-C₃alkylthio, C₁-C₃alkoxycarbonyl, C₁-C₃alkoxycarbonyl-C₁-C₅alkyl, C₅-C₇cycloalkyl, C₂-C₄alkenyl, C₂-C₄alkynyl, benzyl or C₁-C₃halogenoalkyl, or R₇ is C₅-C₇cycloalkenyl, C₅-C₇cycloalkenyl substituted by C₁-C₃alkyl, or R₇ is C₆-C₁₂bicycloalkyl, C₆-C₁₂bicycloalkyl substituted by C₁-C₃alkyl or halogen, C₆-C₁₂bicycloalkenyl, C₆-C₁₂bicycloalkenyl substituted by C₁-C₃alkyl, or R₇ is a substituted or unsubstituted nonaromatic heterocyclic ring of the formula

in which R₁₀₀ and R₁₀₁ are as defined above, or an alicyclic ring system; R₉₀ and R₉₁ independently of one another are hydrogen, C₁-C₁₂alkyl, C₁-C₁₂alkyl substituted by halogen, NO₂, CN, hydroxyl, C₁-C₃alkoxy, C₁-C₃trialkylsilyl, C₁-C₆alkylamino, di(C₁-C₆alkyl)amino, C₃-C₇cycloalkyl,

 or a heterocyclic ring of the formula

in which R₂₅ and R₁₀₀ are as defined above, or R₉₀ and R₉₁ independently of one another are C₃-C₁₀alkenyl, C₃-C₁₀alkynyl, C₆-C₁₂bicycloalkyl, C₆-C₁₂bicycloalkenyl, C₃-C₁₂cycloalkyl, C₃-C₁₂cycloalkyl substituted by C₁-C₄alkyl, C₅-C₇cycloalkenyl or C₅-C₇cycloalkenyl substituted by C₁-C₄alkyl, with the proviso that R₉₀ and R₉₁ are not simultaneously hydrogen; or R₉₀ and R₉₁, together with the nitrogen atom to which they are bonded, form a saturated heterocyclic ring which contains 2-12 carbon atoms and can contain, as further heteroatoms, a nitrogen, an oxygen or a sulfur atom and can be substituted by C₁-C₄alkyl, C₁- or C₂-halogenoalkyl, methoxy-C₁-C₄alkyl, halogen, hydroxyl, CN, C₁-C₄alkoxy, C₁-C₄alkylcarbonyl, C₁- or C₂halogenoalkyl,

 C₁-C₃alkoxycarbonyl, (C₁-C₃alkyl)₂NCO, di(C₁-C₄alkyl)amino or ═O and can additionally be bridged by 1 or 2

 groups and onto which 1 or 2 further carbocyclic, heterocyclic or aromatic rings can be fused, or R₉₀ and R₉₁, together with the nitrogen atom to which they are bonded, form a monounsaturated heterocyclic ring which contains 5-7 carbon atoms and is substituted or unsubstituted by C₁-C₄alkyl, C₁- or C₂halogenoalkyl, halogen, hydroxyl, CN, amino, C₁-C₄alkylamino, di(C₁-C₄alkyl)amino, phenyl, C₁-C₄alkoxy or C₁-C₃alkoxycarbonyl and is additionally bridged by 1 or 2

 groups and onto which 1 or 2 further carbocyclic, heterocyclic or aromatic rings can be fused; the radicals R₂₄ independently of one another are hydrogen or methyl; R₉₈ is hydrogen, fluorine, chlorine, bromine, CN, C₁-C₃alkoxy, C₁-C₃alkoxycarbonyl, C₁-C₃-alkoxy-C₁-C₃alkyl, C₁- or C₂halogenoalkyl, C₁-C₅alkyl, NO₂, C₃-C₅alkenyl, cyclopropyl or C₁- or C₂halogenoalkoxy; R₂ is halogen, C₁-C₁₀alkoxy, C₁-C₁₀alkoxy substituted by halogen, CN, NO₂, C₁-C₆alkoxy, C₁-C₆alkylthio, C₃-C₆alkenyloxy, C₁-C₆alkoxycarbonyl, heterocyclyl of the formula

in which R₂₄, R₉₈, R₁₀₀ and R₁₀₁ are as defined above, or substituted or unsubstituted aryl or aryloxy, C₃-C₁₀alkenyloxy, C₃-C₁₀alkenyloxy substituted by halogen, CN, NO₂, C₁-C₆alkoxy, C₃-C₆alkenyloxy, C₁-C₆alkoxycarbonyl or substituted or unsubstituted aryl or aryloxy, C₁-C₁₀alkylthio, C₁-C₁₀alkylthio substituted by halogen, CN, NO₂, C₁-C₆alkoxy, C₃-C₆alkenyloxy, C₁-C₆alkoxycarbonyl or substituted or unsubstituted aryl or aryloxy, C₃-C₁₀alkenylthio or C₃-C₁₀alkenylthio substituted by halogen, CN, NO₂, C₁-C₆alkoxy, C₃-C₆alkenyloxy, C₁-C₆alkoxycarbonyl or substituted or unsubstituted aryl or aryloxy, or R₂ is C₃-C₅alkynyloxy, C₃-C₅alkynylthio, C₃-C₈oycloalkyl-X—, C₆-C₁₂bicycloalkyl-X—, heterocyclyl-X—, alicyclyl-X—, aryl-X—, phthalidyl-X—, biphenyl-X— or heteroaryl-X—; X is —O—, —S—, —SO— or —SO₂—, or R₂ is a group R₈₈R₈₉N—,

R₈₈ and R₈₉ independently of one another are hydrogen, C₁-C₆alkyl, C₁-C₆alkyl substituted by halogen, CN, C₁-C₃alkoxy or

 C₃-C₁₂cycloalkyl, C₃-C₁₀alkenyl, C₃-C₁₀alkynyl, C₆-C₁₂bicycloalkyl or C₆-C₁₂bicycloalkyl substituted by C₁-C₃alkyl; the radicals R₂₀ independently of one another are hydrogen or C₁-C₄alkyl; n₇ is 4 or 5; Y is —O—, —S—, —NH— or —NR₁₀₁—; R₁₀₁ is C₁-C₄alkyl, C₁-C₄alkylcarbonyl or C₁-C₃alkoxycarbonyl and R₉₈ is as defined above; and R₃ is halogen, C₁-C₁₀alkoxy, C₁-C₁₀alkoxy substituted by halogen, CN, NO₂, C₁-C₆alkoxy, C₁-C₆alkylthio, C₃-C₆alkenyloxy, C₁-C₆alkoxycarbonyl, heterocyclyl of the formula

in which R₂₄, R₉₈, R₁₀₀ and R₁₀₁ are as defined above, or substituted or unsubstituted aryl or aryloxy, C₃-C₁₀alkenyloxy, C₃-C₁₀alkenyloxy substituted by halogen, CN, NO₂, C₁-C₆alkoxy, C₃-C₆alkenyloxy, C₁-C₆alkoxycarbonyl or substituted or unsubstituted aryl or aryloxy, C₁-C₁₀alkylthio, C₁-C₁₀alkylthio substituted by halogen, CN, NO₂, C₁-C₆alkoxy, C₃-C₆alkenyloxy, C₁-C₆alkoxycarbonyl or substituted or unsubstituted aryl or aryloxy, C₃-C₁₀alkenylthio or C₃-C₁₀alkenylthio substituted by halogen, CN, NO₂, C₁-C₆alkoxy, C₃-C₆alkenyloxy, C₁-C₆alkoxycarbonyl or substituted or unsubstituted aryl or aryloxy, or R₃ is C₃-C₅alkynyloxy, C₃-C₅alkynylthio, C₃-C₈cycloalkyl-X—, C₆-C₁₂bicycloalkyl-X—, heterocyclyl-X—, alicyclyl-X—, aryl-X—, phthalidyl-X—, biphenyl-X— or heteroaryl-X—; and X is as defined above.
 3. A compound according to claim 2, in which

in which the radicals R₂₀ independently of one another are hydrogen or C₁-C₄alkyl; R₂₅ is hydrogen, chlorine, methyl or methoxy; R₁₀₀ is hydrogen or C₁-C₃alkyl; Y₁ is —O—, —S— or —NR₃₀; R₃₀ is hydrogen, methyl, C₁-C₃alkylcarbonyl or (C₁-C₃alkyl)₂NCO; n₁ is 1, 2, 3, 4 or 5; n₂ is 0, 1 or 2; and n₃ is a number from 3 to
 10. 4. A compound according to claim 2, in which R₁ is the group —OR₇; and R₂ and R₃ independently of one another are chlorine, C₁-C₁₀alkoxy, C₁-C₁₀alkoxy substituted by halogen, CN, NO₂, C₁-C₆alkoxy, C₁-C₆alkylthio, C₃-C₆alkenyloxy, C₁-C₆alkoxycarbonyl, heterocyclyl of the formula

in which R₂₄, R₉₈, R₁₀₀ and R₁₀₁ are as defined above, or substituted or unsubstituted aryl or aryloxy, C₃-C₁₀alkenyloxy, C₃-C₁₀alkenyloxy substituted by halogen, CN, NO₂, C₁-C₆alkoxy, C₃-C₆alkenyloxy, C₁-C₆alkoxycarbonyl or substituted or unsubstituted aryl or aryloxy, C₁-C₁₀alkylthio, C₁-C₁₀alkylthio substituted by halogen, CN, NO₂, C₁-C₆alkoxy, C₃-C₆alkenyloxy, C₁-C₆alkoxycarbonyl or substituted or unsubstituted aryl or aryloxy, C₃-C₁₀alkenylthio or C₃-C₁₀alkenylthio substituted by halogen, CN, NO₂, C₁-C₆alkoxy, C₃-C₆alkenyloxy, C₁-C₆alkoxycarbonyl or substituted or unsubstituted aryl or aryloxy, or R₂ and R₃ independently of one another are C₃-C₅alkynyloxy, C₃-C₅alkynylthio, C₃-C₈cycloalkyl-X—, C₆-C₁₂bicycloalkyl-X—, heterocyclyl-X—, alicyclyl-X—, aryl-X—, phthalidyl-X—, biphenyl-X— or heteroaryl-X—.
 5. A compound according to claim 2, in which R₁ is the group —OR₇; R₂ is a group R₈₈R₈₉N—,

 and R₃ is aryl-X—, phthalidyl-X—, biphenyl-X—, or heteroaryl-X—.
 6. A compound according to claim 2, in which R₁ is a group —NR₉₀R₉₁ or

in which the radicals R₂₀, R₂₅, R₁₀₀, Y₁, R₃₀, n₁, n₂ and n₃ are as defined in claim 2; R₂ is a group R₈₈R₈₉N—,

 and R₃ is aryl-X—, phthalidyl-X—, biphenyl-X- or heteroaryl-X—.
 7. A compound according to claim 5, in which R₁ is a group —OR₇; R₇ C₁-C₁₆alkyl, C₁-C₁₆alkyl substituted by halogen, NO₂, CN, C₁-C₅alkoxy, C₁-C₅alkylthio, C₁-C₈cycloalkoxy, C₁-C₃trialkylsilyl, C₃-C₁₀alkenyloxy, C₃-C₅alkynyloxy, C₁-C₅alkylcarbonyloxy, C₁-C₃alkoxycarbonyl, C₁-C₃alkylcarbonyl, C₅-C₇cycloalkenyl or C₅-C₇cycloalkenyl substituted by C₁-C₄alkyl, or R₇ is C₁-C₁₆alkyl substituted by C₆-C₁₂bicycloalkyl, C₆-C₁₂chlorobicycloalkyl, C₆-C₁₂bicycloalkenyl or adamantyl, or R₇ is C₁-C₁₆alkyl substituted by

in which R₂₄ is hydrogen or methyl; R₉₈ is hydrogen, fluorine, chlorine, bromine, CN, C₁-C₃alkoxy, C₁-C₃alkoxycarbonyl, C₁-C₃alkoxy-C₁-C₃alkyl, C₁- or C₂halogenoalkyl, C₁-C₅alkyl, NO₂, C₃-C₅alkenyl, cyclopropyl or C₁- or C₂halogenoalkoxy; R₉₉ is hydrogen, halogen, NO₂, CN, C₁-C₅alkyl, C₁-C₆alkoxy, C₁-C₆alkenyloxycarbonyl, C₁-C₃alkylthio,

 C₁-C₆alkoxycarbonyl, NH₂, C₁-C₃alkyl-CONH, di(C₁-C₆alkyl)amino or C₁-C₆alkylamino; R₁₀₀ is hydrogen or C₁-C₃alkyl; and R₁₀₁ is C₁-C₄alkyl, C₁-C₄alkylcarbonyl or C₁-C₃alkoxycarbonyl; or R₇ is C₃-C₁₂cycloalkyl, C₃-C₁₂cycloalkyl substituted by halogen, CN, C₁-C₃trialkylsilyl, ═O, C₁-C₆alkyl, cyano-C₁-C₅alkyl, C₁-C₅alkyl-CONH—C₁-C₅alkyl, phenyl-CONH—C₁-C₅alkyl, C₁-C₅chloroalkyl, C₁-C₃alkoxy, C₁-C₃alkylthio, C₁-C₃alkoxycarbonyl, C₁-C₃alkoxycarbonyl-C₁-C₅alkyl, C₅-C₇cycloalkyl, C₂-C₄alkenyl, C₂-C₄alkynyl, benzyl or C₁-C₃halogenoalkyl, C₅-C₇cycloalkenyl or C₅-C₇cycloalkenyl substituted by C₁-C₃alkyl, or R₇ is C₆-C₁₂bicycloalkyl, C₆-C₁₂bicycloalkyl substituted by C₁-C₃alkyl or halogen, C₆-C₁₂bicycloalkenyl or C₆-C₁₂bicycloalkenyl substituted by C₁-C₃alkyl, or R₇ is a substituted or unsubstituted non-aromatic heterocyclic ring of the formula

in which R₁₀₀ is hydrogen or C₁-C₃alkyl; and R₁₀₁ is C₁-C₄alkyl, C₁-C₄alkylcarbonyl or C₁-C₃alkoxycarbonyl, or R₇ is an alicyclic ring system; R₂ is a group R₈₈R₈₉N—; R₈₈ and R₈₉ independently of one another are hydrogen, C₁-C₆alkyl, C₁-C₆alkyl substituted by halogen, CN, C₁-C₃alkoxy or

 C₃-C₁₂cycloalkyl, C₃-C₁₀alkenyl, C₃-C₁₀alkynyl, C₆-C₁₂bicycloalkyl or C₆-C₁₂bicycloalkyl substituted by C₁-C₃alkyl; and R₃ is aryl-X—, phthalidyl-X—, biphenyl-X— or heteroaryl-X—.
 8. A compound according to claim 7, in which R₇ is C₃-C₁₂cycloalkyl, C₃-C₁₂cycloalkyl substituted by halogen, CN, C₁-C₆alkyl, cyano-C₁-C₅alkyl, C₁-C₃alkoxy or C₁-C₃halogenoalkyl, or R₇ C₅-C₇cycloalkenyl or C₅-C₇cycloalkenyl substituted by methyl, or R₇ is C₆-C₁₂bicycloalkyl, C₆-C₁₂bicycloalkyl substituted by methyl, or chlorine, C₆-C₁₂bicycloalkenyl or C₆-C₁₂bicycloalkenyl substituted by methyl, or

R₁₀₀ and R₁₀₁ are as defined in claim 7; or

in which R₂₀ is hydrogen or C₁-C₄alkyl; R₂₁ and R₂₂ independently of one another are hydrogen or C₁-C₄alkyl; R₂₄ is hydrogen or methyl; R₂₅ is hydrogen, chlorine, methyl or methoxy; R₉₈ is hydrogen, fluorine, chlorine, bromine, CN, C₁-C₃alkoxy, C₁-C₃alkoxycarbonyl, C₁-C₃alkoxy-C₁-C₃alkyl, C₁- or C₂halogenoalkyl, C₁-C₅alkyl, NO₂, C₃-C₅alkenyl, cyclopropyl or C₁- or C₂-halogenoalkoxy; n₆ is 3, 4, 5 or 6; n₉ is 3 or 4; and R₁₀₀ and R₁₀₁ are as defined above; R₂ is a group R₈₈R₈₉N—; R₈₈ and R₈₉ independently of one another are hydrogen or C₁-C₆alkyl; and

in which X is —O— or —S—; X₂ is —O—, —S— or —NR₁₀₀—; R₂₀, R₂₄ and R₁₀₀ are as defined above; R₉₂ is hydrogen or C₁-C₄alkyl; R₉₃ is hydrogen, C₁-C₄alkyl, hydroxyl, C₁-C₄alkoxy or C₁-C₄alkylthio; R₉₇ is hydrogen, halogen, NO₂, CN, C₃-C₆cycloalkoxy, C₁-C₁₀alkyl, C₁-C₁₀alkyl substituted by halogen, CN, NO₂, C₁-C₆alkoxy, C₃-C₆alkenyloxy, C₁-C₆alkoxycarbonyl or substituted or unsubstituted aryl or aryloxy, C₃-C₁₀alkenyl, C₃-C₁₀alkenyl substituted by halogen, CN, NO₂, C₁-C₆alkoxy, C₃-C₆alkenyloxy, C₁-C₆alkoxycarbonyl or substituted or unsubstituted aryl or aryloxy, C₁-C₁₀alkoxy, C₁-C₁₀alkoxy substituted by halogen, CN, NO₂, C₁-C₆alkoxy, C₃-C₆alkenyloxy, C₁-C₆alkoxycarbonyl or substituted or unsubstituted aryl or aryloxy, C₃-C₁₀alkenyloxy, C₃-C₁₀alkenyloxy substituted by halogen, CN, NO₂, C₁-C₆alkoxy, C₃-C₆alkenyloxy, C₁-C₆alkoxycarbonyl or substituted or unsubstituted aryl or aryloxy, C₁-C₁₀alkylcarbonyl, C₁-C₁₀alkylcarbonyl substituted by halogen, CN, NO₂, C₁-C₆alkoxy, C₃-C₆alkenyloxy, C₁-C₆alkoxycarbonyl or substituted or unsubstituted aryl or aryloxy, C₁-C₁₀alkoxycarbonyl, C₁-C₁₀alkoxycarbonyl substituted by halogen, CN, NO₂, C₁-C₆alkoxy, C₃-C₆alkenyloxy, C₁-C₆alkoxycarbonyl or substituted or unsubstituted aryl or aryloxy, C₁-C₁₀alkylcarbonyloxy or C₁-C₁₀alkylcarbonyloxy substituted by halogen, CN, NO₂, C₁-C₆-alkoxy, C₃-C₆alkenyloxy, C₁-C₆alkoxycarbonyl or substituted or unsubstituted aryl or aryloxy, or R₉₇ is CHO, C₃-C₈cycloalkyl, C₁-C₄alkylthio, C₃- or C₄alkenylthio, (R₉₄)₂N—, (R₉₅)₂N—CO—, aryl, aryloxy, arylcarbonyl or aryloxycarbonyl, or a group

 the radicals R₉₄ independently of one another are hydrogen, C₁-C₁₀alkyl, C₃-C₈cycloalkyl, C₁-C₁₀alkylcarbonyl or substituted or unsubstituted arylcarbonyl; the radicals R₉₅ independently of one another are hydrogen, C₁-C₅alkyl or C₃-C₈cycloalkyl; n₅ is a number from 5 to 12; and R₉₈ is as defined above.
 9. A compound according to claim 8, in which X and X₂ are —O—.
 10. A compound according to claim 6, in which R₁ is a group —NR₉₀R₉₁ or

R₉₀ and R₉₁ independently of one another are C₁-C₁₂alkyl, C₁-C₁₂alkyl substituted by halogen, CN or C₁-C₃alkoxy, C₆-C₁₂bicycloalkyl, C₆-C₁₂bicycloalkenyl, C₃-C₁₂cycloalkyl, C₃-C₁₂cycloalkyl substituted by C₁-C₄alkyl, C₅-C₇cycloalkenyl or C₅-C₇cycloalkenyl substituted by C₁-C₄alkyl; the radicals R₂₀ independently of one another are hydrogen or C₁-C₄alkyl; n₁ is 1, 2, 3, 4 or 5; n₂ is 0, 1 or 2; and n₃ is a number from 3 to 10; R₂ is a group R₈₈R₈₉N—; R₈₈ and R₈₉ independently of one another are hydrogen or C₁-C₆alkyl and

in which X is —O—, —S—, —SO— or —SO₂—; X₂ is —O—, —S— or —NR₁₀₀—; R₁₀₀ is hydrogen or C₁-C₃alkyl; R₂₀ is as defined above; R₂₄ is hydrogen or methyl; R₉₂ is hydrogen or C₁-C₄alkyl; R₉₃ is hydrogen, C₁-C₄alkyl, C₁-C₄alkoxy or C₁-C₄alkylthio; R₉₇ is hydrogen, halogen, NO₂, CN, C₃-C₆cycloalkoxy, C₁-C₁₀alkyl, C₁-C₁₀alkyl substituted by halogen, CN, NO₂, C₁-C₆alkoxy, C₃-C₆alkenyloxy, C₁-C₆alkoxycarbonyl or substituted or unsubstituted aryl or aryloxy, C₃-C₁₀alkenyl, C₃-C₁₀alkenyl substituted by halogen, CN, NO₂, C₁-C₆alkoxy, C₃-C₆alkenyloxy, C₁-C₆alkoxycarbonyl or substituted or unsubstituted aryl or aryloxy, C₁-C₁₀alkoxy, C₁-C₁₀alkoxy substituted by halogen, CN, NO₂, C₁-C₆alkoxy, C₃-C₆-alkenyloxy, C₁-C₆alkoxycarbonyl or substituted or unsubstituted aryl or aryloxy, C₃-C₁₀alkenyloxy, C₃-C₁₀alkenyloxy substituted by halogen, CN, NO₂, C₁-C₆alkoxy, C₃-C₆alkenyloxy, C₁-C₆alkoxycarbonyl or substituted or unsubstituted aryl or aryloxy, C₁-C₁₀alkylcarbonyl, C₁-C₁₀alkylcarbonyl substituted by halogen, CN, NO₂, C₁-C₆alkoxy, C₃-C₆alkenyloxy, C₁-C₆alkoxycarbonyl or substituted or unsubstituted aryl or aryloxy, C₁-C₁₀alkoxycarbonyl, C₁-C₁₀alkoxycarbonyl substituted by halogen, CN, NO₂, C₁-C₆alkoxy, C₃-C₆alkenyloxy, C₁-C₆alkoxycarbonyl or substituted or unsubstituted aryl or aryloxy, C₁-C₁₀alkylcarbonyloxy or C₁-C₁₀alkylcarbonyloxy substituted by halogen, CN, NO₂, C₁-C₆-alkoxy, C₃-C₆alkenyloxy, C₁-C₆alkoxycarbonyl or substituted or unsubstituted aryl or aryloxy, or R₉₇ is CHO, C₃-C₈cycloalkyl, C₁-C₄alkylthio, C₃- or C₄alkenylthio, (R₉₄)₂N—, (R₉₅)₂N—CO—, aryl, aryloxy, arylcarbonyl or aryloxycarbonyl, or a group

 the radicals R₉₄ independently of one another are hydrogen, C₁-C₁₀alkyl, C₃-C₈cycloalkyl, C₁-C₁₀alkylcarbonyl or substituted or unsubstituted arylcarbonyl; the radicals R₉₅ independently of one another are hydrogen, C₁-C₅alkyl or C₃-C₈cycloalkyl; n₅ is a number from 5 to 12; and R₉₈ is hydrogen, fluorine, chlorine, bromine, CN, C₁-C₃alkoxy, C₁-C₃alkoxycarbonyl, C₁-C₃-alkoxy-C₁-C₃alkyl, C₁- or C₂halogenoalkyl, C₁-C₅alkyl, NO₂, C₃-C₅alkenyl, cyclopropyl or C₁- or C₂halogenoalkoxy.
 11. A compound according to claim 10, in which R₁ is a group —NR₉₀R₉₁ or

R₉₀ and R₉₁ independently of one another are C₁-C₁₂alkyl, C₁-C₁₂alkyl substituted by halogen, CN or C₁-C₃alkoxy, C₃-C₈cycloalkyl, C₃-C₈cycloalkyl substituted by methyl, C₅-C₇cycloalkenyl or C₅-C₇cycloalkenyl substituted by methyl; the radicals R₂₀ independently of one another are hydrogen or methyl; n₁ is 2, 3 or 4; n₂ is 0 or 1; and n₃ is 3, 4 or 5; R₂ is a group R₈₈R₈₉N—; R₈₈ and R₈₉ independently of one another are hydrogen or C₁-C₃alkyl; and

in which X is —O— or —S—; R₉₇ is hydrogen, halogen, NO₂, CN, C₁-C₁₀alkyl, C₁-C₁₀alkyl substituted by halogen, CN, NO₂, C₁-C₆alkoxy or substituted or unsubstituted aryl or aryloxy, C₃-C₁₀alkenyl, C₃-C₁₀alkenyl substituted by halogen, CN, NO₂, C₁-C₆alkoxy or substituted or unsubstituted aryl or aryloxy, C₁-C₁₀alkoxy, C₁-C₁₀alkoxy substituted by halogen, CN, NO₂, C₁-C₆alkoxy or substituted or unsubstituted aryl or aryloxy, C₃-C₁₀alkenyloxy, C₃-C₁₀alkenyloxy substituted by halogen, CN, NO₂, C₁-C₆alkoxy or substituted or unsubstituted aryl or aryloxy, C₁-C₁₀alkoxycarbonyl, C₁-C₁₀alkoxycarbonyl substituted by halogen, CN, NO₂, C₁-C₆alkoxy or substituted or unsubstituted aryl or aryloxy, C₁-C₁₀alkylcarbonyloxy or C₁-C₁₀alkylcarbonyloxy substituted by halogen, CN, NO₂, C₁-C₆alkoxy or substituted or unsubstituted aryl or aryloxy, or R₉₇ is (R₉₄)₂N—, (R₉₅)₂N—CO—, aryl, aryloxy, arylcarbonyl or aryloxycarbonyl; the radicals R₉₄ independently of one another are hydrogen, C₁-C₄alkyl, C₃-C₈cycloalkyl, C₁-C₅alkylcarbonyl or substituted or unsubstituted arylcarbonyl; and the radicals R₉₅ independently of one another are hydrogen, C₁-C₃alkyl or C₃-C₆cycloalkyl.
 12. A compound according to claim 2, selected from the group consisting of: 3-amino-5-pentafluorophenoxy-1-(trans-3,3,5-trimethylcyclohexanolyl)thiatriazine; 3-amino-5-pentafluorophenoxy-1-[(N-cis-3,3,5-trimethylcyclohexyl)methylamino]thiatriazine; 3-amino-5-pentafluorophenoxy-1-octamethyleneimino-thiatriazine; 3-amino-5-pentafluorophenoxy-1-decahydroquinolyl-thiatriazine; 3-amino-5-pentafluorophenoxy-1-tetrahydroisoquinolyl-thiatriazine; and the compound of the formula


13. A process for the preparation of a compound according to claim 1, in which R₁ is the group —OR₇; R₂ and R₃ independently of one another are halogen, C₁-C₁₀alkoxy, C₁-C₁₀alkoxy substituted by halogen, CN, NO₂, C₁-C₆alkoxy, C₁-C₆alkylthio, C₃-C₆alkenyloxy, C₁-C₆alkoxycarbonyl, heterocyclyl of the formula

 in which R₂₄, R₉₈, R₁₀₀ and R₁₀₁ are as defined in claim 1, or substituted or unsubstituted aryl or aryloxy, C₃-C₁₀alkenyloxy, C₃-C₁₀alkenyloxy substituted by halogen, CN, NO₂, C₁-C₆alkoxy, C₃-C₆alkenyloxy, C₁-C₆alkoxycarbonyl or substituted or unsubstituted aryl or aryloxy, C₁-C₁₀alkylthio, C₁-C₁₀alkylthio substituted by halogen, CN, NO₂, C₁-C₆alkoxy, C₃-C₆alkenyloxy, C₁-C₆alkoxycarbonyl or substituted or unsubstituted aryl or aryloxy, C₃-C₁₀alkenylthio or C₃-C₁₀alkenylthio substituted by halogen, CN, NO₂, C₁-C₆alkoxy, C₃-C₆alkenyloxy, C₁-C₆alkoxycarbonyl or substituted or unsubstituted aryl or aryloxy, or R₂ and R₃ independently of one another are C₃-C₅alkynyloxy, C₃-C₅alkynylthio, C₃-C₈cycloalkyl-X—, C₆-C₁₂bicycloalkyl-X—, heterocyclyl-X—, alicyclyl-X—, aryl-X—, phthalidyl-X—, biphenyl-X— or heteroaryl-X—, and X is as defined in claim 1, which comprises a procedure in which a₁) 1,3,5-trichlorothiatriazine is converted with an alcohol of the formula XVII R₇—OH  (XVII),  in which R₇ is as defined in claim 1 if appropriate in the presence of an equimolar amount of base and an inert organic solvent, into the compound of the formula VII

 in which R₇ is as defined, and this compound is then either b₁) reacted with a compound of the formula XXIII R₁₄—X₁H  (XXIII),  in which R₁₄ is C₁-C₁₀alkyl, C₁-C₁₀alkyl substituted by halogen, CN, NO₂, C₁-C₆alkoxy, C₁-C₆alkylthio, C₃-C₆alkenyloxy, C₁-C₆alkoxycarbonyl, heterocyclyl of the formula

 in which R₂₄, R₉₈, R₁₀₀ and R₁₀₁ are as defined in claim 1, or substituted or unsubstituted aryl or aryloxy, C₃-C₁₀alkenyl or C₃-C₁₀alkenyl substituted by halogen, CN, NO₂, C₁-C₆alkoxy, C₃-C₆alkenyloxy, C₁-C₆alkoxycarbonyl or substituted or unsubstituted aryl or aryloxy, C₃-C₅alkynyl, C₃-C₈cycloalkyl, C₆-C₁₂bicycloalkyl, heterocyclyl of the formula

 in which R₂₄, R₁₀₀ and R₁₀₁ are as defined above, or alicyclyl, and X₁ is oxygen or sulfur, in the presence of an equimolar amount of base and an inert organic solvent, or b₂) converted with a compound of the formula XVI R₁₂—X₁H  (XVI),  in which R₁₂ is an aryl, phthalidyl, biphenyl or heteroaryl radical; and X₁ is oxygen or sulfur, in the presence of an equimolar amount of base and an aprotic solvent, into the compound of the formula VI

 in which R₃ is —X₁—R₁₂, and this compound is either c₂) reacted with the compound of the formula XXIII R₁₄—X₁H  (XXIII),  in which R₁₄ and X₁ are as defined above, in the presence of an equimolar amount of base and an inert organic solvent, or c₃) converted with the compound of the formula XVI R₁₂—X₁H  (XVI),  in which R₁₂ and X₁ are as defined above, in the presence of an equimolar amount of base and an aprotic solvent, into the compound of the formula V

 in which R₃ is —X₁—R₁₂ and R₇, X₁ and R₁₂ are as defined above, and this compound is then d₃) reacted with the compound of the formula XXIII R₁₄—X₁H  (XXIII),  in which R₁₄ and X₁ are as defined, in the presence of an equimolar amount of base and in an inert organic solvent, or the compound of the formula VII b₃) is converted with 2 mol of compound of the formula XVI R₁₂—X₁H  (XVI),  in which R₁₂ and X₁ are as defined, in the presence of an equimolar amount of base and in an aprotic organic solvent, into the compound of the formula V, and this compound is then reacted in a manner analogous to that described under d₃), or a₂) 1,3,5-trichlorothiatriazine is converted with a C₆-C₁₂bicycloalkyl epoxide, a C₆-C₁₂bicycloalkyl epoxide substituted by C₁-C₃alkyl or an epoxide of the formula XVIII or XIX

 in which the radicals R₁₃ independently of one another are hydrogen, C₃-C₈alkenyl, C₁-C₁₄alkyl, C₁-C₁₄alkyl substituted by halogen, NO₂, CN, C₁-C₅alkoxy, aryloxy or C₁-C₃alkoxycarbonyl; the radicals R₂₃ independently of one another are hydrogen or C₁-C₆alkyl; n₈ is a number from 3-10; and n₁₁ is 1 or 2, in an inert organic solvent, into the compound of the formula VII in which R₇ is C₂-C₁₆-β-chloroalkyl, C₂-C₁₆-β-chloroalkyl substituted by halogen, NO₂, CN, C₁-C₅alkoxy, aryloxy or C₁-C₃alkoxycarbonyl, C₅-C₁₂-β-chlorocycloalkyl or C₅-C₁₂-β-chlorocycloalkyl substituted by C₁-C₆alkyl, and this compound is reacted further in a manner analogous to that described under b₁); b₂) and c₂); b₂), c₃) and d₃); or b₃) and d₃), or a₃) 1,3,5-trichlorothiatriazine is reacted with an alcohol of the formula XVII R₇—OH  (XVII),  in which R₇ is C₁-C₁₀alkyl, C₁-C₁₀alkyl substituted by halogen, CN, NO₂, C₁-C₅alkoxy, C₁-C₅alkylthio, C₃-C₆alkenyloxy, C₁-C₃alkoxycarbonyl, heterocyclyl of the formula

 in which R₂₄, R₉₈, R₁₀₀ and R₁₀₁ are as defined in claim 1, or substituted or unsubstituted aryl or aryloxy, C₃-C₁₀alkenyl, C₃-C₁₀alkenyl substituted by halogen, C₁-C₃alkoxy or substituted or unsubstituted aryl or aryloxy, C₃-C₅alkynyl, C₃-C₈cycloalkyl, C₆-C₁₂bicycloalkyl, a heterocyclic ring of the formula

 in which R₁₀₀ and R₁₀₁ are as defined above, or alicyclyl, if appropriate in an inert solvent in the presence of an eqimolar amount of base.
 14. A process for the preparation of a compound according to claim 1, in which R₁ is the group —OR₇;  R₂ is a group R₈₈R₈₉N—,

and R₃ is aryl-X—, phthalidyl-X—, biphenyl-X— or heteroaryl-X—, which comprises a procedure in which c₄) a compound of the formula VI

 in which R₇ is as defined in claim 1 and R₃ is as defined above, is reacted with an amine of the formula XIII, XIV or XV R₈₈R₈₉NH   (XIII),

in which R₂₀, R₈₈, R₈₉, Y and n₇ are as defined in claim 1, if appropriate in a solvent; or c₃) the compound of the formula VI is first converted with a compound of the formula XVI R₁₂—X₁H  (XVI),  in which R₁₂ is an aryl, phthalidyl, biphenyl or heteroaryl radical, and X₁ is oxygen or sulfur, in the presence of an equimolar amount of base and in an aprotic organic solvent, into the compound of the formula V

 in which R₃ is —X₁—R₁₂ and R₇, R₁₂ and X₁ are as defined, and d₄) this is then reacted with an amine of the formula XIII, XIV or XV in a manner analogous to that described under C₄); or in which a₄) 1,3,5-trichlorothiatriazine is converted with an alcoholate of the formula XVII₁ (R₇O—O⁻)_(n) M₁ ^(+n)  (XVII₁),  in which R₇ is as defined in claim 1; M₁ ^(+n) is an alkali metal or alkaline earth metal ion or a metal ion of the first or second sub-group of the Periodic Table; and n is 1, 2, 3 or 4, in the presence of an inert organic solvent, into the compound of the formula VII

 in which R₇ is as defined, and b₄) this is reacted with an amine of the formula XIII, XIV or XV R₈₈R₈₉NH   (XIII),

in which R₂₀, R₈₈, R₈₉, Y and n₇ are as defined in claim 1, if appropriate in a solvent, to give the compound of the formula VIII

 in which R₂ and R₇ are as defined, and c₅) this is then reacted with a compound of the formula XVI R₁₂—X₁H  (XVI),  in which R₁₂ is an aryl, phthalidyl, biphenyl or heteroaryl radical; and X₁ is oxygen or sulfur, in a solvent in the presence of a tertiary amine and, if appropriate, another base.
 15. A process for the preparation of a compound according to claim 1, in which R₁ is a group —NR₉₀R₉₁ or R₁ is

 in which the radicals R₂₀ independently of one another are hydrogen, C₁-C₄alkyl or C₁-C₃alkoxy; R₂₅ is hydrogen, chlorine, methyl or methoxy; R₁₀₀ is hydrogen or C₁-C₃alkyl; Y₁ is —O—, —S— or —NR₃₀; R₃₀ is hydrogen, methyl, C₁-C₃alkylcarbonyl or (C₁-C₃alkyl)₂NCO; n₁ is 1, 2, 3, 4 or 5; n₂ is 0, 1 or 2; and n₃ is a number from 3 to 10; R₂ is a group R₈₈R₈₉N—,

 and R₃ is aryl-X—, phthalidyl-X—, biphenyl-X— or heteroaryl-X—, which comprises a procedure in which e) a compound of the formula III

 in which R₇ is as defined in claim 1 and R₂ and R₃ are as defined, is reacted with an amine of the formula XI or XII

 in which R₉₀ and R₉₁ are as defined in claim 1 and R₁₁ is a cyclic radical onto which 1 or 2 further carbocyclic, heterocyclic or aromatic rings can be fused and which can contain further heteroatoms, if appropriate in a solvent; or in which a₅) 1,3,5-trichlorothiatriazine is converted with an amine of the formula XI or XII

 in which R₉₀ and R₉₁ are as defined in claim 1 and R₁₁ is a cyclic radical onto which 1 or 2 carbocyclic, heterocyclic or aromatic rings can be fused and which can contain further heteroatoms, or with an amide of the formula XI, or XII₁

 in which R₉₀, R₉₁ and R₁₁ are as defined; M₂ ^(+n) is an alkali metal or alkaline earth metal ion or a metal ion of the first or second sub-group of the Periodic Table; and n is 1, 2, 3 or 4, in the presence of an inert organic solvent and if appropriate a base, into the compound of the formula IX

 in which R₁ is as defined, and b₅) this is reacted with an amine of the formula XIII, XIV or XV R₈₈R₈₉NH   (XIII),

in which R₂₀, R₈₈, R₈₉, Y and n₇ are as defined in claim 1, if appropriate in a solvent, to give the compound of the formula X

 in which R₁ and R₂ are as defined, and c₆) this is then reacted with a compound of the formula XVI R₁₂-X₁H  (XVI),  in which R₁₂ is an aryl, phthalidyl, biphenyl or heteroaryl radical; and X₁ is oxygen or sulfur, in a solvent in the presence of a tertiary amine and a further equivalent amount of base.
 16. A process for the preparation of a compound according to claim 1, in which R₁ is a group —OR₇; R₂ is a group R₈₈R₈₉N—,

 aryl-X—, phthalidyl-X—, biphenyl-X— or heteroaryl-X—; and R₃ is aryl-X—, phthalidyl-X—, biphenyl-X— or heteroaryl-X—, which comprises a procedure in which a compound of the formula I, in which R₁ is a group —OR₇, in which R₇ is other than in the end product; and R₂ and R₃ are as defined, is reacted with an alcohol of the formula XVII R₇—OH  (XVII), in which R₇ is other than in the starting substance of the formula I, in the presence of an inert organic solvent and a catalytic or equimolar amount of base.
 17. A compound of the formula VII

 in which R₇ is as defined in claim
 1. 18. A compound of the formula VI

 in which R₇ is as defined in claim 1, R₃ is aryl-X—, phthalidyl-X—, biphenyl-X— or heteroaryl-X—, and X is as defined in claim
 1. 19. A compound of the formula V

 in which R₇ is as defined in claim 1, R₃ is aryl-X—, phthalidyl-X—, biphenyl-X— or heteroaryl-X—, and X is as defined in claim
 1. 20. A compound of the formula VIII

 in which R₂ is a group R₈₈R₈₉N—,

 and R₇, R₂₀, R₈₈, R₈₉, Y and n₇ are as defined in claim
 1. 21. A compound of the formula IX

 in which R₁is a group R₉₀R₉₁N— or

R₉₀ and R₉₁ are as defined in claim 1; and R₁₁ is a cyclic radical onto which 1 or 2 carbocyclic, heterocyclic or aromatic rings can be fused and which can contain further heteroatoms, excluding the compounds


22. A compound of the formula X

 in which R₁ is a group R₉₀R₉₁N— or

 and R₂i s a group R₈₈R₈₉N—,

 and R₂₀, R₈₈, R₈₉, R_(90, R) ₉₁, Y and n₇ are as defined in claim 1; and R₁₁ is a cyclic radical onto which 1 or 2 carbocyclic, heterocyclic or aromatic rings can be fused and which can contain further heteroatoms, excluding the compounds

wherein R₀₁ is hydrogen, methyl, ethyl, n-propyl, i-butyl, tert-butyl, allyl, cyclohexyl or benzyl; R₀₂ is ethyl or i-butyl, R₀₃ is cyclohexyl or i-butyl; and R₀₂ and R₀₃ together with the nitrogen atom to which they are bonded, form a piperidine ring.
 23. A herbicidal or plant growth-inhibiting composition, which comprises a compound according to claim 1, in a herbicidal or plant growth-inhibiting effective amount, and an inert carrier.
 24. The composition according to claim 23, in which the compound comprises between 0.1% and 95% of the composition.
 25. A method of controlling undesirable plant growth, which comprises applying to the plants, in a herbicidally effective amount, the compound according to claim 1 to the plants or their environment.
 26. The method according to claim 25, wherein an amount of between 0.001 and 4 kg of the compound per hectare is applied to the plants.
 27. A method of inhibiting plant growth, which comprises applying a compound according to claim 1 in an effective inhibiting amount to the plants or their environment. 